Water → HCID 23003353, compound

Participants

Reaction Steps

To a stirred solution of thiazole (0.11 g, 1.23 mmol) in diethyl ether (4 ml) was added n-BuLi (1.55M in hexane, 0.79ml) at −78° C. under nitrogen atmosphere. After stirring for 30 min., zinc chloride (1.0M in diethyl ether, 3.7 ml, 3.7 mmol) was added, and the mixture stirred at 0° C. for 30 min. To the resulting mixture was added palladium catalyst prepared in THF (5 ml) by the treatment of a suspension of dichlorobis(triphenylphosphine)palladium(II) (0.22 g, 0.31 mmol) with n-BuLi (1.55M in hexane, 0.39 ml). Methyl[6-chloro-2-(4-bromobenzoyl)-1H-indol-3-yl]acetate (Example 206, 0.25 g, 0.61 mmol) was added to the mixture. The reaction mixture was heated at reflux temperature for 4 h., poured into water (50 ml), and extracted with ethyl acetate (50 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4), and concentrated. This crude product was purified by flash column chromatography eluting with ethyl acetate-hexane (1:3) to afford 0.18 g (72%) of the title compound as yellow solids.

Provenance & Evidence