Butyl vinyl ether → HCID 16073198, compound

Participants

Reaction Conditions

Reaction Steps

Preparation of compound 49(a) (6-acetyl-2-(4-fluoro-phenyl)-5-isopropoxy-benzofuran-3-carboxylic acid methylamide). A sealed tube was charged with magnetic stirrer, compound 24(b) (1.22 g, 3.0 mmol, which can be prepared according to Example 24, step b above), palladium(II) acetate (34 mg, 0.015 mmol), [1,1′-bis(diphenylphosphino)propane] (DPPP) (136 mg, 0.33 mmol), butyl vinyl ether (1.92 mL, 15 mmol), and K2CO3 (622 mg, 4.5 mmol) in DMF (5 mL). The tube was flushed with argon, sealed, and heated to 100° C. for 24 hours, then cooled to room temperature. 5% HCl (20 mL) was added dropwise over 20 minutes, and the mixture with extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 20% ethyl acetate in hexanes) to yield 0.94 g (85%) of the desired product.

Provenance & Evidence