5-Bromo-3-pyridinemethanol

5-Bromo-3-pyridinemethanol serves as a precursor for synthesizing [3-(benzyloxy)methyl]-5-bromopyridine via reaction with sodium hydride and benzyl bromide[6].

Sodium borohydride (2.2 g, 59.1 mmol) was added to a suspension of 5-bromo-pyridine-3-carbaldehyde (10.0 g, 53.7 mmol) in MeOH (100 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour before it was quenched by adding water (5.0 mL). Evaporation of solvents afforded a light yellowish oil, which was re-dissolved in EtOAc and washed with water. The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 5-Bromo-3-pyridinemethanol (9.6 g, 95 per cent) as a colourless oil.

[1] Patent: WO2013/79452,  2013,  A1. Location in patent: Page/Page column 143
[2] Patent: US2013/143863,  2013,  A1. Location in patent: Paragraph 1076; 1077; 1078
[3] Journal of Medicinal Chemistry,  2016,  vol. 59,  # 10,  p. 4913 - 4925
[4] Patent: US2013/267495,  2013,  A1. Location in patent: Paragraph 0454-0455
[5] Patent: US2013/296302,  2013,  A1. Location in patent: Paragraph 0549
[6] Kelly, T. R., Howard, H. R., Koe, B. K., & Sarges, R. (1985). Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]. Journal of Medicinal Chemistry, 28(9), 1368–1371. https://doi.org/10.1021/jm00147a046