Potassium Carbonate → 4-Benzyloxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester

Participants

Reaction Steps

A mixture of 4-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester (207 mg, 0.5 mmol, see example D-86a), Pd(PPh3)4 (58 mg, 0.05 mmol), 2-methylpropylboronic acid (78 mg, 0.75 mmol), K2CO3 (207 mg, 1.5 mmol), and 1,4-dioxane (4 ml) was refluxed with stirring for 48 h. Subsequently, the mixture was concentrated in vacuo. To the residue was added water (5 ml) and the mixture was extracted with EtOAc (2×20 ml). The organic phase was dried over MgsO4 and evaporated in vacuo. Purification of the residue by flash column chromatography on silica gel using hexanes EtOAc=88 12 as the eluent gave the title compound as a yellowish oil (136 mg); MS-(+)-ion M+1=392.3.

Provenance & Evidence