Water → HCID 66649106, compound

Participants

Reaction Steps

To a solution of (2-(dimethylamino)ethyl)triphenylphosphonium bromide (680 mg, 1.54 mmol) in THF (7.7 mL) was added n-BuLi (2.5M in hexanes, 0.65 mL, 1.62 mmol) dropwise at 0° C., the resulting mixture was warmed to room temperature and stirred for 30 min. 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbaldehyde 233 (500 mg, 1.17 mmol) was added in one portion and the mixture was stirred for 2 h. The mixture was poured into water, extracted with EtOAc; the organic phase was extracted with 3% citric acid, the combined aqueous phase was basified to pH˜11 by the addition of 1N NaOH. It was then extracted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure affording title compound 234 (360 mg, 0.929 mmol, 78% yield) as a crude mixture that was used in the next step without further purification. MS (m/z): (M+1) 388.1 (100%).

Provenance & Evidence