Production Method 1

55289-36-6

25015-63-8

882678-96-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  2-(Dicyclohexylphosphino)biphenyl Catalysts: Palladium diacetate Solvents: 1,4-Dioxane ;  1 h, 80 °C

Reference

The identification of 2-(1H-indazol-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (GDC-0941) as a potent, selective, orally bioavailable inhibitor of class I PI3 kinase for the treatment of cancer

Folkes, Adrian J.; et al, Journal of Medicinal Chemistry, 2008, 51(18), 5522-5532

Production Method 2

55289-35-5

73183-34-3

882678-96-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: 1,1-Bis(diphenylphosphino)ferrocene ,  [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  5 h, reflux
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  6 h, rt

Reference

Structure-Based Drug Design of RN486, a Potent and Selective Bruton's Tyrosine Kinase (BTK) Inhibitor, for the Treatment of Rheumatoid Arthritis

Lou, Yan; et al, Journal of Medicinal Chemistry, 2015, 58(1), 512-516

Production Method 3

55289-36-6

73183-34-3

882678-96-8

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  2.75 h, 110 °C

Reference

Discovery of Branebrutinib (BMS-986195): A Strategy for Identifying a Highly Potent and Selective Covalent Inhibitor Providing Rapid in Vivo Inactivation of Bruton's Tyrosine Kinase (BTK)

Watterson, Scott H. ; et al, Journal of Medicinal Chemistry, 2019, 62(7), 3228-3250

Production Method 4

55289-35-5

882678-96-8

Reaction Conditions

1.1 -
2.1 Reagents: Hydrogen Catalysts: Platinum dioxide Solvents: Tetrahydrofuran ;  2 h, rt

Reference

1,4,6-Trisubstituted imidazo[4,5-c]pyridines as inhibitors of Bruton's tyrosine kinase

Krajcovicova, Sona; et al, European Journal of Medicinal Chemistry, 2021, 211,

2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Raw materials

• 1-Bromo-2-methyl-3-nitrobenzene
• 3-Bromo-2-methylaniline
• Bis(pinacolato)diborane
• Pinacolborane

2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Preparation Products

• 2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (882678-96-8)

• 1. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 2. An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes?
  Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
• 3. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 4. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642
• 5. An analysis of the WTC fires using CIB correlations and simple modeling
  JGQuintiere

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aminotoluenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Toluenes Aminotoluenes

• 195062-59-0(4,4,5,5-Tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane)
• 356570-53-1(2-(2,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1256360-31-2(3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 850567-52-1(3-Amino-4-methylphenylboronic acid, pinacol ester, hydrochloride)
• 882670-69-1(4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 325141-72-8(2-(2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 631909-35-8(3-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Benzenamine)
• 303006-89-5(2,5-Dimethyl-1,4-phenylenediboronic acid, pinacol ester)
• 1004761-68-5(4-Amino-3,5-dimethylphenylboronic Acid Pinacol Ester)
• 631911-01-8(4-Amino-2-methylphenylboronic Acid Pinacol Ester)