1-Bromo-4-fluorobenzene → HCID 58975036, compound

Participants

Reaction Conditions

Reaction Steps

Add 1-bromo-4-fluorobenzene (220 μL, 350 mg, 2.0 mmol, 2.0 equiv) to a mixture of (3-aminomethyl-azetidin-1-yl)-[4-(3-phenyl-indole-1-sulfonyl)-phenyl]-methanone (446 mg, 1.00 mmol, 1 equiv), tris(dibenzylideneacetone)dipalladium(0) (23 mg, 0.025 mmol, 0.025 equiv), 2-(di-tert-butylphosphino)biphenyl (15 mg, 0.057 mmol, 0.050 equiv), and sodium tert-butoxide (120 mg, 1.2 mmol, 1.2 equiv) in anhydr toluene (4 mL) and heat at 100° C. for 19 h. After cooling, transfer the reaction mixture through a 0.45-μm filter disc to a column of silica gel (125 mm×25 mm dia.) and elute (10-100% EtOAc/hex) to yield 98 mg (18%) of [3-[(4-fluoro-phenylamino)-methyl]-azetidin-1-yl]-[4-(3-phenyl-indole-1-sulfonyl)-phenyl]-methanone as a light-yellow foam. 1H NMR indicated pure desired product. MS (m/e): 540.07 (M+1); 538.19 (M−1).

Provenance & Evidence