Potassium Carbonate → HCID 22601722, compound

Participants

Reaction Conditions

Reaction Steps

2-[3-Bromo-5-(4-methoxyphenyl)-4-methylthien-2-yl]-1,3-dioxolane (7.0 g, 20 mmol), 3-methoxyphenylboronic acid (3.3 g, 22 mmol), K2CO3 (9.1 g, 66 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium [II] (0.8 g, 1 mmol) were combined in 20% aqueous dimethoxyethane (80 mL) and heated at 75° C. After 8 h, the cooled mixture was filtered through Celite and washed with ethyl acetate (200 mL). The filtrate was washed with 1 N aqueous NaOH and brine (200 mL each), dried (K2CO3) and concentrated in vacuo to give the crude product (8.4 g) as a dark oil which was pre-adsorbed on silica gel (15 g). Flash chromatography (105 g silica, gradient 5%-10%-20% ethyl acetate-hexane) gave the title compound (7.2 g, 95%) as a clear, colorless oil.

Provenance & Evidence