Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9]1([S:15]([OH:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CCOC(C)=O.[Cu]I.CS(C)=O>[C:9]1([S:15]([C:2]2[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1To 5-bromopyridin-3-amine (1.59 g, 9.19 mmol) (Aldrich) was added benzenesulfinic acid, sodium salt (1.810 g, 11.03 mmol) (Sigma-Aldrich), copper(I) iodide (0.175 g, 0.919 mmol), (S)-pyrrolidine-2-carboxylic acid (0.212 g, 1.838 mmol), sodium hydroxide (0.074 g, 1.838 mmol), and DMSO (18 mL), and the resulting mixture was stirred at 100° C. for 3 days. The reaction mixture was then diluted with 200 mL of EtOAc, added to a separatory funnel, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was separated, washed 4 times with 150 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 3% (2 M ammonia in MeOH)/DCM) furnished the title compound (11% yield). m/z (ESI, +ve ion) 235.3 (M+H)+.
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