Acrylamide → HCID 86591781, compound

Participants

Reaction Conditions

Reaction Steps

Sodium acetate was dissolved in water (0.5 mL). The carboxylic acid methyl ester builiding lock III, e.g. methyl{[(4-bromophenyl)sulfonyl]-4-methylanilino}acetate (398 mg, 1 mmol), in DMW (3.5 mL) was added, followed by acrylamide (78 mg, 1.11 mmol), triphenylphosphine (26.2 mg, 0.11 mmol, 10 mol %) and palladium diacetate (11.2 mg, 0.05 mmol, 5 mol %). The resulting mixture was degazed for 5 min with argon and was heated at 80° C. for 3 h. It was filtrated through celite. Water (5 mL) was added and the desired product was extracted with ethyl acetate (3×7 mL). Combined organic phases were dried over magnesium sulfate before filtering and removal of solvent The desired product, e.g. methyl[({4-[(1E)-3-amino-3-oxo-1-propenyl]phenyl}sulfonyl)-4-methylanilino]acetate was obtained as a colorless oil, in 88% purity by HPLC (MaxPlot detection between 230 and 400 nm). This intermediate was used in the next step without further purification.

Provenance & Evidence