反应详情

温度

100 °C

A glass microwave reaction vessel was charged with 5-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)-2-pyridinamine (318 mg, 0.88 mmol), 2-(2-chloro-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (100 mg, 0.44 mmol, Intermediate E), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (18 mg, 0.02 mmol, Strem Chemical Inc, Newburyport, Mass.), cesium carbonate (431 mg, 1.32 mmol, Sigma-Aldrich, St. Louis, Mo.), DME (1.5 mL), and water (0.2 mL). The reaction mixture was purged with nitrogen for several minutes, and then stirred and heated in an Emrys Optmizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 45 min. The organic layer was taken and the solvent was removed under vacuum. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a silica gel column (12 g), eluting with a gradient of DCM to 3% 2M NH3.MeOH in DCM, to provide 2-(2-(4-((6-amino-3-pyridinyl)sulfonyl)phenyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (70 mg) as an off-white solid and a mixture of enantiomers.

1. customA glass microwave reaction vessel
2. customThe reaction mixture was purged with nitrogen for several minutes
3. customthe solvent was removed under vacuum
4. customThe crude material was absorbed onto a plug of silica gel
5. custompurified by chromatography through a silica gel column (12 g)
6. washeluting with a gradient of DCM to 3% 2M NH3