Aniline → tert-butyl 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

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Reaction Steps

Tris(dibenzylideneacetone)dipalladium(0) (20 mg, 022 mmol, 0.020 equiv) was added to a deoxygenated mixture of tert-butyl 3-(2-chloro-5-fluorophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate (1-2,330 mg, 1.11 mmol, 1 equiv), benzenediazonium tetrafluoroborate (1-3, prepared from aniline by the method described for 1-1, 213 mg, 1.11 mmol, 1.00 equiv), and sodium acetate trihydrate (459 mg, 3.32 mmol, 3.00 equiv) in acetonitrile (20 mL) at 23° C. The reaction mixture was stirred for 16 h, then partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (2×70 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes initially, grading to 40% hexanes in EtOAc) to provide tert-butyl 4-(2-chloro-5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (14) as a dark orange oil. LRMS m/z (M+H—CH3) 359.0 found, 359.1 required.

Provenance & Evidence