Ethyl (2E)-3-(6-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate → ethyl 3-(6-cyano-5-fluoro-1H-indol-3-yl)propanoate

HRID 1512850Notes

Reaction equation

HRID 1512850 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][NH:9]2)=[CH:5][C:4]=1[F:19])#[N:2]>CO.[Pd]>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][NH:9]2)=[CH:5][C:4]=1[F:19])#[N:2]

Participants

4

Reactant 1

HCID 67094393Ethyl (2E)-3-(6-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate

Product 1

HCID 67025270ethyl 3-(6-cyano-5-fluoro-1H-indol-3-yl)propanoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl (2E)-3-(6-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate (D153) (200 mg) in methanol (30 mL) was added 10% Pd/C (50 mg). The reaction mixture was then stirred under H2 overnight. The solution was filtered through celite and the filtrate was evaporated to give the designed product ethyl 3-(6-cyano-5-fluoro-1H-indol-3-yl)propanoate (D154) (190 mg). MS (ES): C14H13FN2O2 requires 260.1; found 261.1 (M+H+).

Workup

  1. filtrationThe solution was filtered through celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d6b5cc9199a247abac0f60829185471d
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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