118289-16-0

White to brown powder

2-Bromo-4-hydroxymethylpyridine is used to synthesize aza- and diazabiphenyl analogs of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824). It is also used to N3/8-disubstituted 3,8-diazabicyclo[3.2.1]octane analogues of 3,8-bis[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl-piperazine with antiproliferative properties.

Contact with 2-Bromopyridine-4-methanol causes skin irritation and serious eye irritation.

General procedure for the synthesis of 2-bromo-4-pyridinemethanol from 2-bromo-4-pyridinecarboxylic acid: To a solution of tetrahydrofuran (30 mL) containing 2-bromo-4-pyridinecarboxylic acid (2 g, 9.9 mmol, 1.0 eq.) was added drop-wise the boron trifluoride ether compound (4.18 g, 29.7 mmol, 3.0 eq.) at 0 °C. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction mixture was transferred to ice water and the product was extracted with ethyl acetate. The organic layers were combined, washed with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-bromo-4-pyridine methanol (1.4 g, 75.21% yield). Mass spectrum (electrospray): m/z 189.65 [M]+.

[1] Patent: WO2018/71794, 2018, A1. Location in patent: Paragraph 00983; 00984
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2866 - 2875
[4] Patent: US2005/54654, 2005, A1. Location in patent: Page/Page column 36
[5] Patent: EP2098517, 2009, A1. Location in patent: Page/Page column 32