Production Method 1

115666-21-2

86915-22-2

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt; rt → 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  1 h, 0 °C

Reference

Organocatalytic Formal (3+2) Cycloaddition toward Chiral Pyrrolo[1,2-a]indoles via Dynamic Kinetic Resolution of Allene Intermediates

Bai, Jian-Fei; et al, Organic Letters, 2020, 22(14), 5439-5445

Production Method 2

242805-94-3

86915-22-2

Reaction Conditions

1.1 Reagents: tert-Butanol ,  Water Solvents: Tetrahydrofuran
1.2 Solvents: Water
1.3 Solvents: Diethyl ether

Reference

Directed C-7 lithiation of 1-(2,2-diethylbutanoyl)indoles

Fukuda, Tsutomu; et al, Tetrahedron, 1999, 55(30), 9151-9162

Production Method 3

51417-51-7

86915-22-2

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  5 min, 0 °C; 2 h, 0 °C → 40 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  40 °C; 1 h, 40 °C → 90 °C
1.3 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  10 min, 0 °C; overnight, rt
1.4 Reagents: Water ;  rt
1.5 Reagents: Sodium hydroxide Solvents: Water ;  rt
1.6 Reagents: Water ;  15 min, rt

Reference

Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2-a]indoles

Xie, Tao; et al, Journal of Organic Chemistry, 2021, 86(8), 5518-5529

Production Method 4

14092-04-7

86915-22-2

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  -45 °C; 30 min, -45 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  -45 °C; -45 °C → rt

Reference

Bidentate P, N-P Ligand for Nickel-Catalyzed Cross-Coupling of Aryl or Benzyl Chlorides with ArMgX

Ghosh, Raju; et al, Journal of Organic Chemistry, 2010, 75(23), 8283-8286

Production Method 5

1730-25-2

86915-22-2

Reaction Conditions

Reference

Structure-Activity Relationship Studies Leading to the Identification of (2E)-3-[l-[(2,4-Dichlorophenyl)methyl]-5-fluoro-3-methyl-1H-indol-7-yl]-N-[(4,5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a Potent and Selective Prostanoid EP3 Receptor Antagonist, as a Novel Antiplatelet Agent That Does Not Prolong Bleeding

Singh, Jasbir; et al, Journal of Medicinal Chemistry, 2010, 53(1), 18-36

Production Method 6

50709-33-6

86915-22-2

Reaction Conditions

1.1 Solvents: Acetic acid ;  overnight, 100 °C

Reference

Chiral-Phosphoric-Acid-Catalyzed C6-Selective Pictet-Spengler Reactions for Construction of Polycyclic Indoles Containing Spiro Quaternary Stereocenters

Wang, Xin-Wei ; et al, Organic Letters, 2022, 24(8), 1727-1731

Production Method 7

83-34-1

35354-15-5

86915-22-2

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
1.2 -
1.3 Reagents: Ammonium chloride Solvents: Water
1.4 Solvents: Diethyl ether
2.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Solvents: Diethyl ether
2.2 Reagents: 1,2-Dibromo-1,1,2,2-tetrafluoroethane
2.3 Reagents: Ammonium chloride Solvents: Water
2.4 Solvents: Diethyl ether
3.1 Reagents: tert-Butanol ,  Water Solvents: Tetrahydrofuran
3.2 Solvents: Water
3.3 Solvents: Diethyl ether

Reference

Directed C-7 lithiation of 1-(2,2-diethylbutanoyl)indoles

Fukuda, Tsutomu; et al, Tetrahedron, 1999, 55(30), 9151-9162

Production Method 8

51417-51-7

86915-22-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Triphenylphosphine ,  Cobalt bis(tetrafluoroborate) hexahydrate Solvents: Methanol ;  24 h, 100 °C

Reference

Methylation of C(sp3)-H/C(sp2)-H Bonds with Methanol Catalyzed by Cobalt System

Liu, Zhenghui; et al, Organic Letters, 2017, 19(19), 5228-5231

Production Method 9

51417-51-7

86915-22-2

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: 2885997-69-1 Solvents: Methanol ;  24 h, 110 °C

Reference

α-Methylation of Ketones and Indoles Catalyzed by a Manganese(I) PCNHCP Pincer Complex with Methanol as a C1 Source

Thenarukandiyil, Ranjeesh; et al, Organometallics, 2023, 42(1), 62-71

Production Method 10

51417-51-7

86915-22-2

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide ,  Oxygen Catalysts: Iridium, di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopen… Solvents: Methanol ;  17 h, 140 °C

Reference

Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Chen, Shu-Jie; et al, RSC Advances, 2015, 5(86), 70329-70332

Production Method 11

115666-21-2

86915-22-2

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  15 min, 0 °C; overnight, rt

Reference

2-alkylation of 3-alkyindoles with unactivated alkenes

Pan, Xuling; et al, Frontiers in Chemistry (Lausanne, 2022, 10,

Production Method 12

51417-51-7

86915-22-2

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  30 min, 0 °C; 2 h, 40 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  40 °C; 1 h, 90 °C
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  15 min, 0 °C; overnight, rt

Reference

2-alkylation of 3-alkyindoles with unactivated alkenes

Pan, Xuling; et al, Frontiers in Chemistry (Lausanne, 2022, 10,

Production Method 13

14092-04-7

86915-22-2

Reaction Conditions

1.1 Solvents: Tetrahydrofuran
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Total Synthesis of Indoles from Tricholoma Species via Bartoli/Heteroaryl Radical Methodologies

Dobbs, Adrian, Journal of Organic Chemistry, 2001, 66(2), 638-641

Production Method 14

1803607-41-1

86915-22-2

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Catalysts: Iridium, di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopen… Solvents: Methanol ;  44 h, 60 °C

Reference

Ir(III)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles

Kim, Youyoung; et al, Chemical Communications (Cambridge, 2021, 57(92), 12309-12312

Production Method 15

16732-66-4

86915-22-2

Reaction Conditions

1.1 Solvents: Dichloromethane ;  10 min, rt
1.2 Reagents: Zinc chloride Solvents: p-Xylene ;  20 min, 160 °C; 160 °C

Reference

Visible Light-Mediated C-H Difluoromethylation of Electron-Rich Heteroarenes

Su, Yi-Ming; et al, Organic Letters, 2014, 16(11), 2958-2961

Production Method 16

86915-15-3

86915-22-2

Reaction Conditions

1.1 Reagents: Borane Catalysts: Tetrahydrofuran

Reference

A versatile and efficient process to 3-substituted indoles from anilines

Wierenga, Wendell; et al, Tetrahedron Letters, 1983, 24(24), 2437-40

Production Method 17

242805-87-4

86915-22-2

Reaction Conditions

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Solvents: Diethyl ether
1.2 Reagents: 1,2-Dibromo-1,1,2,2-tetrafluoroethane
1.3 Reagents: Ammonium chloride Solvents: Water
1.4 Solvents: Diethyl ether
2.1 Reagents: tert-Butanol ,  Water Solvents: Tetrahydrofuran
2.2 Solvents: Water
2.3 Solvents: Diethyl ether

Reference

Directed C-7 lithiation of 1-(2,2-diethylbutanoyl)indoles

Fukuda, Tsutomu; et al, Tetrahedron, 1999, 55(30), 9151-9162

7-Bromo-3-methyl-1H-indole Raw materials

• 2-Bromophenylhydrazine hydrochloride
• 7-Bromo-1H-indole
• 7-bromo-1H-indole-3-carbaldehyde
• (2-Bromophenyl)hydrazine
• Allylmagnesium Bromide (ca. 13% in Ethyl Ether, ca. 0.7mol/L)
• 1-Propenylmagnesium bromide
• 1-Butanone, 1-(7-bromo-3-methyl-1H-indol-1-yl)-2,2-diethyl-
• 3,7-Dibromo-1,3-dihydro-3-methyl-2H-indol-2-one
• Skatole
• 1-Butanone, 2,2-diethyl-1-(3-methyl-1H-indol-1-yl)-
• Benzenamine, 2-bromo-6-(1-methylethenyl)-
• Butanoyl chloride, 2,2-diethyl-

7-Bromo-3-methyl-1H-indole Preparation Products

• 7-Bromo-3-methyl-1H-indole (86915-22-2)

• 1. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
• 2. Enantiomorphic symmetry breaking in crystallization of molten sodium chlorate?
  Martin R. Ward,Gary W. Copeland,Andrew J. Alexander Chem. Commun., 2010,46, 7634-7636
• 3. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 4. Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging
  Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario Giordano Analyst, 2018,143, 4674-4683
• 5. Emerging investigator series: kinetics of diopside reactivity for carbon mineralization in mafic–ultramafic rocks
  BrianaAguila,LandonHardee,H.ToddSchaef,SiavashZare,MohammadJavadAbdolhosseiniQomi,JarrodV.Crum,JadeE.HollimanJr.,ElenaTajueloRodriguez,LawrenceM.Anovitz,KevinM.Rosso,QuinR.S.Miller

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives 3-alkylindoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles 3-alkylindoles

• 660867-81-2(Cyclohepta[b]pyrrole, 8-bromo-3-phenyl-)
• 172939-50-3(8-Bromo-4-methylquinoline)
• 903131-21-5(3-bromo-7-methyl-1H-indole)
• 165669-07-8(7-Bromo-4-methyl-1H-indole)
• 823803-51-6(8-bromo-5-methylquinoline)
• 887581-42-2((7-bromo-1H-indol-3-yl)methanamine)
• 10075-48-6(5-Bromo-3-methyl-1h-indole)
• 18073-34-2(9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole)
• 1043601-50-8(7-bromo-1h-indole-3-carbonitrile)
• 1219741-50-0(6-Bromo-3-methyl-1H-indole)