Water → Ammonia

Participants

Reaction Conditions

Reaction Steps

Prepare three microwavable reaction vials containing 3-bromo-thieno[3,2-b]pyridine (214 mg, 1.0 mmol) and methylboronic acid (180 mg, 3.0 mmol) in DME/water/EtOH=7/3/1 (4 mL). Add 2 M Na2CO3 (1.5 mL, 3.0 mmol) and bubble in nitrogen gas for 15 min. Add Pd(PPh3)4 (58 mg, 0.05 mmol) and seal the vials. Heat the vials at 130° C. for 30 min in the microwave. Combine all the reaction mixtures, add water and CH2Cl2 and extract. Separate the CH2Cl2 layer, dry over Na2SO4, filter, and evaporate. Purify the resulting material using silica gel chromatography, eluting with hexane:ethyl acetate: 2 M NH3 in MeOH=20:4:1, to give the title compound (193 mg, 43%. ES/MS m/z 150 (M+1)+.

Provenance & Evidence