[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([CH:15]=O)[C:10]=1[F:17].C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl.CCOC(C)=O>[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](/[CH:15]=[N:7]/[S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[C:10]=1[F:17]A solution of (R)-2-methylpropane-2-sulfinamide (0.540 g, 4.32 mmol), 4-chloro-3-fluoropicolinaldehyde (0.627 g, 3.93 mmol) and Cs2CO3 (1.921 g, 5.89 mmol) in DCM (20 mL) was stirred for 1 h at rt. The reaction mixture was diluted with EtOAc and washed with brine (3×20 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to provide the desired product (1.1 g, 100%). MS (ESI) m/z: 263.0 (M+H)+.
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