1-Bromo-4-fluorobenzene → HCID 58975060, compound

Participants

Reaction Conditions

Reaction Steps

Add 1-bromo-4-fluorobenzene (110 μL, 180 mg, 1.0 mmol, 2.0 equiv) to a mixture of N-azetidin-3-yl-4-(3-phenyl-indole-1-sulfonyl)-benzamide (216 mg, 0.501 mmol, 1 equiv), tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.012 mmol, 0.025 equiv), 2-(di-tert-butylphosphino)biphenyl (8 mg, 0.03 mmol, 0.05 equiv), and sodium tert-butoxide (58 mg, 0.60 mmol, 1.2 equiv) in anhydr toluene (2 mL). Heat the reaction mixture at 100° C. for 14 h. After cooling, dilute the reaction mixture with CH2Cl2 and transfer through a 0.45-μm filter disc to a column of silica gel (80 mm×20 mm dia.) and elute (10-35% EtOAc/hex) to yield 63 mg (24%) of N-[1-(4-fluoro-phenyl)-azetidin-3-yl]-4-(3-phenyl-indole-1-sulfonyl)-benzamide as a white solid.

Provenance & Evidence