Trityl chloride → 3-(4-Bromothiazol-2-yl)-1-trityl-pyrazolo[5,4-b]pyridine

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[S:5][CH:6]=1.[H-].[Na+].Cl[C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:8]=2)[S:5][CH:6]=1

Participants

Procedure

A solution of 3-(4-bromothiazol-2-yl)-1H-pyrazolo[5,4-b]pyridine (161 mg, 0.5727 mmol) in DMF (3 mL) was cooled to 0° C. then sodium hydride (27.49 mg, 0.6872 mmol) was added in one portion. Stirred at 0° C. for 30 mins before (chloro-diphenyl-methyl)benzene (167.6 mg, 0.6013 mmol) was added. Ice-bath removed and stirred at room temperature for 2 h. Quenched with water, diluted with EtOAc. Organic layer then collected, washed with brine, dried (MgSO4), filtered and concentrated in vacuo.