Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:12])OC.O[C@H]1C[NH:17][C@H:16]([C:19](O)=O)[CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(N)(C)C>[Cu]I.CS(C)=O>[CH:16]([N:17]1[C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH:8][C:9]1=[O:12])([CH3:19])[CH3:15]A sealed tube was charged with methyl 3-bromopyridin-4-ylcarbamate (1.76 g, 7.6 mmol.), CuI (290 mg, 1.52 mmol.), trans-4-hydroxy-L-proline (400 mg, 3.04 mmol.) and K3PO4 (3.2 g, 15.2 mmol.), evacuated and backfilled with argon. Isopropylamine (674 mg, 11.4 mmol.) and DMSO (15 mL) were added successively. The reaction mixture was stirred at 70° C. for 12 h and then at 130° C. for 12 h. The reaction mixture filtered and the filtrate was concentrated and purified by prep-HPLC to afford 3-isopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one (765 mg, 57%).
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