Acetic Acid → (4-Amino-6-bromopyridin-2-yl)methanol

Participants

Reaction Steps

A solution of 6-bromo-4-nitro-pyridine-2-carboxylic acid (example 6a) (6.60 g, 29.1 mmol) in THF (150 ml) was treated with borane/THF (87 ml of a 1M solution). The mixture was refluxed for 6 hr, then powdered iron (16.3 g, 291 mmol) was added, followed by acetic acid (150 ml). Reflux was maintained for 6 hr, the mixture was filtered, evaporated and partitioned (AcOEt/NaHCO3-solution). The organic phase was dried (Na2SO4), concentrated and chromatographed (SiO2 with CH2Cl2/MeOH=93/7) to provide 2.0 g (34%) of (4-amino-6-bromo-pyridin-2-yl)-methanol as a white solid material. Mp. 144-145° C. (AcOEt), MS: m/e=202 (M+).

Provenance & Evidence