Ethyl (2E)-3-(7-cyano-6-fluoro-1H-indol-3-yl)-2-propenoate → ethyl 3-(7-cyano-6-fluoro-1H-indol-3-yl)propanoate

HRID 1512841Notes

Reaction equation

HRID 1512841 reaction equation
[C:1]([C:3]1[C:4]([F:19])=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:2]>C1COCC1.Cl[Pd]Cl>[C:1]([C:3]1[C:4]([F:19])=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:2]

Participants

4

Reactant 1

HCID 59146028Ethyl (2E)-3-(7-cyano-6-fluoro-1H-indol-3-yl)-2-propenoate

Product 1

HCID 59146069ethyl 3-(7-cyano-6-fluoro-1H-indol-3-yl)propanoateYield 92.1%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2E)-3-(7-cyano-6-fluoro-1H-indol-3-yl)-2-propenoate (D143) (1.8 g) in THF (50 mL) was added PdCl2 (0.5 g). The reaction was stirred under H2 (15 psi) atmosphere at RT for about 5 hours. TLC showed the starting material was completely consumed. Then PdCl2 was removed by filtration, the filtrate was concentrated and washed with PE to afford ethyl 3-(7-cyano-6-fluoro-1H-indol-3-yl)propanoate (D144) (1.67 g) as a white solid. δH (DMSO-d6, 400 MHz): 1.15 (3H, t), 2.66 (2H, t), 2.93 (2H, t), 4.03 (2H, q), 7.08 (1H, dd), 7.28 (1H, s), 7.93 (1H, dd), 11.90 (1H, s); MS (ES): C14H13FN2O2 requires 260; found 261.2 (M+H+).

Workup

  1. customwas completely consumed
  2. customThen PdCl2 was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. washwashed with PE

Sources & evidence

ORD record
ord-5da4202851c4419d916e585a7cd4c684
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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