Methanol--water (1/1) → Thienopyridine

Participants

Reaction Conditions

Reaction Steps

Dissolve 7-bromo-thieno[3,2-b]pyridine (3.69 g, 17 mmol) in dry THF (20 mL) and cool to −78° C. Add n-BuLi (1.6 M in hexane, 21.2 mL, 34 mmol) slowly to the mixture at −78° C. and stir at −78° C. for 20 min. Add MeOH/H2O=1/1 (20 mL) and stir at room temperature for 1 h. Extract the reaction mixture with CH2Cl2. Wash the organic portion with saturated NaCl solution, dry over Na2SO4, and evaporate. Purify the resulting residue using silica gel chromatography, eluting with 100% hexane to hexane:ethyl acetate=10:1 to give the title compound (1.44 g, 62%). ES/MS m/z 136 (M+1)+.

Provenance & Evidence