Potassium Carbonate → HCID 68525583, compound

Reaction equation

Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31][CH3:32])[CH2:27][CH2:26]3)=[O:24])=[CH:19][CH:18]=2)=[CH:14][CH:15]=1)=[O:8].Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31][CH2:32][CH2:38][C:39]4[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=4)[CH2:27][CH2:26]3)=[O:24])=[CH:21][CH:22]=2)=[CH:14][CH:15]=1)=[O:8]

Participants

Procedure

3,4-dichloro-N-{6-[4-(4-methylamino-piperidine-1-carbonyl)phenoxy]pyridin-3-yl}benzamide dihydrochloride (114 mg, 0.2 mmol) was dissolved in DMF (3 mL). To the resulting solution were added 4-bromomethyl-1,2-difluorobenzene (31 μl, 0.24 mmol) and potassium carbonate (111 mg, 0.8 mmol), and this solution was stirred for 4 hours at room temperature. The resulting reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. This residue was purified by silica gel column chromatography (chloroform:methanol=50:1), to thereby yield 60 mg of the title compound.