Reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22](/[CH:25]=[N:26]/[NH:27][C:28]2[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][N:29]=2)[CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>>[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([C:25]2[N:29]4[CH:30]=[CH:31][C:32]([I:34])=[CH:33][C:28]4=[N:27][N:26]=2)[CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]Participants
3
Procedure
To (E)-tert-butyl(1-(2-((2-(4-iodopyridin-2-yl)hydrazono)methyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (178 mg, 0.304 mmol) was added iodobenzene diacetate (IBD) (127 mg, 0.395 mmol). The reaction was stirred for 2 hours. Additional IBD (0.5 eq) was added and the reaction was stirred for another 2 hours and then quenched with saturated Na2S2O3 (5 mL). The organic layer was extracted with DCM, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography (EtOAc/Hexane/MeOH 2:1:0.1) to provide the final product.
Workup
- stirringthe reaction was stirred for another 2 hours
- customquenched with saturated Na2S2O3 (5 mL)
- extractionThe organic layer was extracted with DCM
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude material was purified by silica gel chromatography (EtOAc/Hexane/MeOH 2:1:0.1)
Sources & evidence
- ORD record
- ord-3d3ae3d7a8964504ac31314a2227c392
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895550B2
Linked notes
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