Piperidine → HCID 59190180, compound

HRID 1645266Notes

Reaction equation

HRID 1645266 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11]([C:13]1[O:17][C:16]([C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1)=O.N1CCCCC1>CCO>[O:10]=[C:2]1[NH:1][C:9]2[C:4](/[C:3]/1=[CH:11]\[C:13]1[O:17][C:16]([C:18]3[CH:19]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:14]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 7183217HCID 7183217, compound

Product 1

HCID 59190180HCID 59190180, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of oxindole (235 mg, 1.76 mmol), tert-butyl 3-(5-formylfuran-2-yl)phenylcarbamate (500 mg, 1.74 mmol) and piperidine (0.18 mL, 1.80 mmol) in EtOH (5.0 mL) was stirred at rt overnight. The resulting precipitate was collected by filtration to yield desired (E)-tert-butyl 3-(5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)phenylcarbamate (640 mg). LCMS (ES): m/z 403 [M+1]+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0e47a2d9175c45eb82d9fc45db42a254
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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