Cesium carbonate → HCID 66582331, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL vial was charged with 5-((4-bromophenyl)sulfonyl)-2-pyridinamine (71 mg, 0.23 mmol), 1,1,1-trifluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (86 mg, 0.27 mmol, synthesized in manner analogous to Example 21 using 2-(4-bromophenyl)-1,1,1-trifluoro-2-propanol (example 27)), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride, dichloromethane complex (18 mg, 0.02 mmol, Sigma-Aldrich, St. Louis, Mo.), and cesium carbonate (222 mg, 0.68 mmol) were combined in DME (1.2 mL) and water (0.1 mL). The reaction mixture was purged with nitrogen for several minutes, and then stirred and heated in an Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 30 min. The organic layer was taken and the solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by column chromatography (12 g of silica gel, 0 to 3% 2M NH3 in MeOH/CH2Cl2) to provide 2-(4′-((6-amino-3-pyridinyl)sulfonyl)-4-biphenylyl)-1,1,1-trifluoro-2-propanol (83 mg) as an off-white solid.

Provenance & Evidence