Borohydride → HCID 11249362, compound

Reaction equation

[BH4-].[CH3:2][N:3]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]1[SH:14].I[C:16]1[CH:35]=[CH:34][C:19]([CH2:20][NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][CH:23]=2)=[C:18]([O:36][CH2:37][CH2:38][CH3:39])[CH:17]=1>O1CCCC1.C(O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][CH2:20][C:19]2[CH:34]=[CH:35][C:16]([S:14][C:4]3[N:3]([CH3:2])[C:7]([C:8]4[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=4)=[N:6][N:5]=3)=[CH:17][C:18]=2[O:36][CH2:37][CH2:38][CH3:39])=[CH:23][CH:24]=1)[CH3:33]

Participants

Procedure

265 mg (0.66 mmol, 3 eq) of resin-supported borohydride and 3 mg (0.01 mmol, 0.03 eq) of bis(bipyridine)dibromonickel (II) are added to a solution of 64 mg (0.33 mmol, 1.5 eq) of 4-methyl-5-pyridin-4-yl-4H-[1,2,4]-triazole-3-thiol in 1.5 ml of tetrahydrofuran/ethanol 5/5. To the suspension obtained there is added a solution of 100 mg (0.22 mmol, 1 eq) of ethyl [4-(4-iodo-2-propoxybenzylamino)phenyl]acetate in 1.5 ml of tetrahydrofuran/ethanol 5/5. The reaction mixture is stirred overnight under reflux. After returning to room temperature, the reaction medium is filtered and then concentrated. 0.111 g (97%) of the expected compound is recovered.