[Cl:1][C:2]1[N:7]=[C:6]2[C:8](I)=[N:9][N:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1.Cl[C:14]1[CH:15]=CC2[C:18](=[C:20](I)[N:21]([CH3:23])N=2)[N:19]=1.CN1CCNCC1.N1CCC[C@H]1C(O)=O>[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([N:19]3[CH2:14][CH2:15][N:21]([CH3:23])[CH2:20][CH2:18]3)=[N:9][N:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1
To a solution of 5-chloro-3-iodo-1-methyl-1H-pyrazolo[4,3-b]pyridine (104 mg, 0.354 mmol, containing the isomer 5-chloro-3-iodo-2-methyl-2H-pyrazolo[4,3-b]pyridine (360 mg, 1.22 mmol) was added 1-methylpiperazine (184 mg, 1.84 mmol), CuI (70 mg, 0.368 mmol), L-proline (84 mg, 0.736 mmol). The reaction mixture was heated at 100° C. for 4 h. The reaction was cooled, washed by sat. NaHCO3, extracted with EtOAc, dried over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C12H16ClN5: 266.1 (M+H+); Found: 266.2 (M+H+).
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