Ethyl Acetate → HCID 68428125, compound

Participants

Reaction Steps

To a mixture of 7-bromo-2,3-dichloro-4-hydroxy-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (1.16 g, 2.74 mmol), 1,1′-bis(diphenylphosphino)ferrocene (228 mg, 0.411 mmol), zinc dust (32.1 mg, 0.493 mmol), and zinc cyanide (290 mg, 2.47 mmol) in N,N-dimethylacetamide (8.7 mL) was added tris(dibenzylideneacetone)dipalladium(0)(188 mg, 0.21 mmol). The reaction mixture was heated at 120° C. for 1.5 hours before ethyl acetate (100 mL) was added. The organic solution was washed with saturated ammonium chloride aqueous solution and saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-30% ethyl acetate in hexanes to produce 0.65 g of the title compound as a light yellow solid. MS: (+) m/z 370.2 (M+1).

Provenance & Evidence