Triethylamine → (2-Bromopyridin-3-yl)methanol

Temperatur

0 °C

To a solution of 2-bromonicotinic acid (4.0 g, 20 mmol) and triethylamine (3.34 mL, 24 mmol, 1.2 eq.) in THF (100 mL) was added i-butyl chloroformate (3.12 mL, 24 mmol, 1.2 eq.) at 0° C. The mixture was stirred at 0° C. for 10 min and filtered. To this filtrate was added a suspension of NaBH4 (1.52 g, 40 mmol, 2 eq.) in water (1.0 mL) at 0° C. The mixture was stirred for 30 min, added water (3 mL), continued to stir for 2 h, and concentrated to dryness. The crude was purified on silica gel using a mixture of ethylacetate and hexanes as eluent to give (2-bromopyridin-3-yl)methanol (3.4 g, 90%) as a white solid. LRMS (M+H+) m/z 188.0.

1. filtrationfiltered
2. additionTo this filtrate was added
3. stirringThe mixture was stirred for 30 min
4. stirringto stir for 2 h
5. concentrationconcentrated to dryness
6. customThe crude was purified on silica gel using
7. additiona mixture of ethylacetate and hexanes as eluent

ORD-Eintrag

ord-f8cf047a6c194398bba655cb354ad5c3

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09018210B2