Potassium Carbonate → HCID 68579599, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-ethyl-4-[(4-methoxyphenyl)sulfonyl]-4,5-dihydrothieno[3,2-c]isoquinoline (1.02 g, 2.2 mmol), 3-thiopheneboronic acid (0.37 g, 2.9 mol), potassium carbonate (0.91 g, 6.6 mol) and [1.1′-bis(diphenylphosphino)ferrocene]dichloropalladium [II] (90 mg, 0.11 mmol) were combined in 40% aqueous dimethoxyethane (11 mL) and the mixture was heated to 75° C. After 3.5 h the mixture was cooled to 23° C., filtered through Celite and washed with ethyl acetate (125 mL). The filtrate was washed with 1 N aqueous sodium hydroxide and brine (125 mL each), dried (K2CO3), and concentrated in vacuo to give the crude product (0.91 g) as a tan solid which was taken up in methylene chloride (ca. 3 mL) and pre-adsorbed on silica gel (3 g). Flash chromatography on silica gel (27 g) eluting 25-, and then 50% methylene chloride-hexane gave the title compound (0.73 g, 71%, m.p. 182-84° C.) as a white solid which was pure enough for further use.

Provenance & Evidence