1-methyl-2-(tributylstannyl)-1H-pyrrole → 1-[3-(1-methyl-1H-pyrrol-2-yl)phenyl]-N-(Pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide
반응식
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[Sn](CCCC)(CCCC)CCCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1참가 물질
4
실험 절차
A mixture of 1-(3-bromophenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (85 mg, 0.209 mmol), Pd(PPh3)2Cl2 (28 mg, 0.040 mmol) and Ag2O (45 mg, 0.196 mmol) was added in one portion to a flask charged with 1-methyl-2-tributylstannanyl-1H-pyrrole (0.391 g, 1.06 mmol). The flask was evacuated and backfilled with N2 (2×) then charged with anhydrous DMF (3.0 mL). After stirring at rt for 5 min the reaction mixture was heated to 90° C. under N2 for 2 d. Later, the reaction was cooled to rt and treated with 1 M aq KF (3 mL) and stirred overnight at rt. Then filtered through Celite (using MeOH to rinse the Celite) and purified by MDPS to provide the product as a white solid. MS (ES+): m/z 408.46 (100) [MH+].