Production Method 1

7194-78-7

81316-36-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ;  rt; 20 min, rt

Reference

Charge Dispersion and Its Effects on the Reactivity of Thiamin-Derived Breslow Intermediates

Bielecki, Michael; et al, Biochemistry, 2018, 57(26), 3867-3872

Production Method 2

24999-51-7

81316-36-1

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

Reductive condensation of methyl arylglyoxylates. Direct synthesis of 2,3-bis(carbomethoxy)stilbene oxides and related systems

Muller, A. J.; et al, Journal of Organic Chemistry, 1982, 47(12), 2342-52

Production Method 3

1711-09-7

81316-36-1

Reaction Conditions

1.1 -
2.1 Reagents: Hydrochloric acid

Reference

Reductive condensation of methyl arylglyoxylates. Direct synthesis of 2,3-bis(carbomethoxy)stilbene oxides and related systems

Muller, A. J.; et al, Journal of Organic Chemistry, 1982, 47(12), 2342-52

Production Method 4

2142-63-4

81316-36-1

Reaction Conditions

1.1 Reagents: Selenium dioxide Solvents: Pyridine ;  10 - 20 h, 120 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Dicyclohexylcarbodiimide Solvents: Dichloromethane ;  12 h

Reference

Umpolung Reactivity of Imine Ester: Visible-Light Mediated Transfer Hydrogenation of α-Aryl Imino Esters by Phenylsilane and Water

Wu, Wei; et al, Chemistry - A European Journal, 2022, 28(68),

Production Method 5

2142-63-4

81316-36-1

Reaction Conditions

1.1 Reagents: Selenium dioxide Solvents: Pyridine ;  overnight, reflux
2.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ;  rt; 20 min, rt

Reference

Charge Dispersion and Its Effects on the Reactivity of Thiamin-Derived Breslow Intermediates

Bielecki, Michael; et al, Biochemistry, 2018, 57(26), 3867-3872

Production Method 6

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 7

1603-40-3

1878-67-7

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
2.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 8

1003-03-8

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen ,  Tetrabutylammonium hydrogen sulfate Catalysts: Cupric acetate Solvents: Acetonitrile ;  6 h, 80 °C
2.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
3.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 9

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen ,  Tetrabutylammonium hydrogen sulfate Catalysts: Cupric acetate Solvents: Acetonitrile ;  6 h, 80 °C
2.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
3.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 10

100-51-6

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C
2.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
3.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 11

1017324-23-0

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen ,  Tetrabutylammonium hydrogen sulfate Catalysts: Cupric acetate Solvents: Acetonitrile ;  6 h, 80 °C
2.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
3.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 12

264882-03-3

81316-36-1

Reaction Conditions

1.1 Reagents: Diethyl azodicarboxylate ,  Water Catalysts: Dirhodium tetraacetate Solvents: Toluene ;  1 h, reflux; 3 h, reflux; reflux → rt

Reference

Facile synthesis of aryl α-keto esters via the reaction of aryldiazoacetate with H2O and DEAD

Guo, Zhenqiu; et al, Synlett, 2006, (15), 2486-2488

Production Method 13

860771-95-5

81316-36-1

Reaction Conditions

1.1 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane ;  rt

Reference

Chiral β-diketonate ligands of 'pseudo planar chiral' topology: enantioselective synthesis and transition metal complexation

Bocknack, Brian M.; et al, Tetrahedron, 2005, 61(26), 6266-6275

Production Method 14

2142-63-4

81316-36-1

Reaction Conditions

1.1 Reagents: Selenium dioxide Solvents: Pyridine ;  rt; 20 h, 110 °C
1.2 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  0 °C; 2 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

Liu, Yonggui; et al, Angewandte Chemie, 2020, 59(1), 442-448

Production Method 15

7194-78-7

81316-36-1

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Dichloromethane ;  12 h

Reference

Umpolung Reactivity of Imine Ester: Visible-Light Mediated Transfer Hydrogenation of α-Aryl Imino Esters by Phenylsilane and Water

Wu, Wei; et al, Chemistry - A European Journal, 2022, 28(68),

Production Method 16

98042-29-6

81316-36-1

Reaction Conditions

1.1 Solvents: Dimethyl sulfoxide ;  overnight, 75 °C; 75 °C → rt
1.2 Solvents: Methanol ;  overnight, rt

Reference

High-Potency Phenylquinoxalinone Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activators

Son, Jung-Ho; et al, Journal of Medicinal Chemistry, 2017, 60(6), 2401-2410

Production Method 17

2142-63-4

81316-36-1

Reaction Conditions

1.1 Reagents: Bromine Solvents: 1,4-Dioxane ;  3 h, rt
2.1 Solvents: Dimethyl sulfoxide ;  overnight, 75 °C; 75 °C → rt
2.2 Solvents: Methanol ;  overnight, rt

Reference

High-Potency Phenylquinoxalinone Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activators

Son, Jung-Ho; et al, Journal of Medicinal Chemistry, 2017, 60(6), 2401-2410

Production Method 18

71412-88-9

81316-36-1

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  6 h, 80 °C
1.2 Reagents: Sulfuric acid Solvents: Methanol ;  2 h, reflux
2.1 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane ;  rt

Reference

Chiral β-diketonate ligands of 'pseudo planar chiral' topology: enantioselective synthesis and transition metal complexation

Bocknack, Brian M.; et al, Tetrahedron, 2005, 61(26), 6266-6275

Production Method 19

3132-99-8

81316-36-1

Reaction Conditions

1.1 Reagents: Sodium bisulfite Solvents: Water ;  2.5 h, rt; rt → 0 °C
1.2 Solvents: Water ;  45 min, 0 °C; 2 h, 0 °C → rt
2.1 Reagents: Hydrochloric acid Solvents: Water ;  6 h, 80 °C
2.2 Reagents: Sulfuric acid Solvents: Methanol ;  2 h, reflux
3.1 Reagents: Manganese oxide (MnO2) Solvents: Dichloromethane ;  rt

Reference

Chiral β-diketonate ligands of 'pseudo planar chiral' topology: enantioselective synthesis and transition metal complexation

Bocknack, Brian M.; et al, Tetrahedron, 2005, 61(26), 6266-6275

Production Method 20

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen ,  Tetrabutylammonium hydrogen sulfate Catalysts: Cupric acetate Solvents: Acetonitrile ;  6 h, 80 °C
2.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
3.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Production Method 21

81316-36-1

1603-40-3

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C
2.1 Reagents: 1-Hydroxybenzotriazole ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Tetrahydrofuran ;  overnight, 25 °C
3.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,2-Dichloroethane ;  6 h, 80 °C

Reference

Copper-Catalyzed Transamidation of Unactivated Secondary Amides via C-H and C-N Bond Simultaneous Activations

Lv, Cong; et al, Journal of Organic Chemistry, 2023, 88(4), 2140-2157

Methyl 2-(3-bromophenyl)-2-oxoacetate Raw materials

• 3-Bromobenzoyl chloride
• Methyl 2-(3-bromophenyl)-2-hydroxyacetate
• 3-Bromobenzaldehyde
• 2-(3-Bromophenyl)-2-hydroxyacetonitrile
• 3-methylpyridin-2-amine
• 3-bromobenzoyl cyanide
• Benzyl alcohol
• 2-(3-Bromophenyl)-2-oxoacetic acid
• 3-Bromophenylacetic acid
• cyclopentanamine
• 3'-Bromoacetophenone
• Ethanone, 2,2-dibromo-1-(3-bromophenyl)-
• Benzeneacetic acid, 3-bromo-α-diazo-, methyl ester
• Benzeneacetamide, 4-methyl-N-(3-methyl-2-pyridinyl)-

Methyl 2-(3-bromophenyl)-2-oxoacetate Preparation Products

• 3-methylpyridin-2-amine (1603-40-3)
• Methyl 2-(3-bromophenyl)-2-oxoacetate (81316-36-1)

• 1. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents
  Craig A. Kelly,David R. Rosseinsky Phys. Chem. Chem. Phys., 2001,3, 2086-2090
• 2. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 3. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 4. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 5. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)