Ethyl (2E)-3-(5-cyano-1H-indol-2-yl)-2-propenoate → ethyl 3-(5-cyano-1H-indol-2-yl)propanoate

HRID 1512744Notes

Reaction equation

HRID 1512744 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6]2)#[N:2]>CO.CCOC(C)=O.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6]2)#[N:2]

Participants

5

Reactant 1

HCID 67025185Ethyl (2E)-3-(5-cyano-1H-indol-2-yl)-2-propenoate

Product 1

HCID 67025284ethyl 3-(5-cyano-1H-indol-2-yl)propanoateYield 99.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl (2E)-3-(5-cyano-1H-indol-2-yl)-2-propenoate (D29) (200 mg) in methanol (40 mL) and EtOAc (20 mL) was hydrogenated using the H-cube (full mode) with a large 10% Pd—C catcart (flow rate: 2.5 mL/min). The solvent was evaporated to afford ethyl 3-(5-cyano-1H-indol-2-yl)propanoate (D30) (200 mg) as a white solid. MS (ES): C14H14N2O2 requires 242; found 243.2 (M+H+).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6a9ddd9792ca4676825528d1ad0fc610
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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