Reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8]/[N:9]=[CH:10]/[C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[C:14]([N:21]4[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][CH2:22]4)[CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:3]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>>[I:1][C:2]1[CH:7]=[CH:6][N:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([N:21]5[CH2:22][CH2:23][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:25][CH2:26]5)[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:8]=[C:4]2[CH:3]=1Participants
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-a814a3eba049463b9495d190a571ece9
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557809B2
Linked notes
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