ethyl (2E)-3-(7-cyano-4-fluoro-1H-indol-3-yl)-2-propenoate → ethyl 3-(7-cyano-4-fluoro-1H-indol-3-yl)propanoate

HRID 1512757Notes

Reaction equation

HRID 1512757 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:19])=[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.[Pd]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:19])=[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 59146086ethyl (2E)-3-(7-cyano-4-fluoro-1H-indol-3-yl)-2-propenoate

Product 1

HCID 59146182ethyl 3-(7-cyano-4-fluoro-1H-indol-3-yl)propanoateYield 59.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl (2E)-3-(7-cyano-4-fluoro-1H-indol-3-yl)-2-propenoate (D43) (10.0 g) in THF (100 mL) under H2 (30 psi) atmosphere was hydrogenated by using the catalyst of Pd/C (with 50% water, 3.0 g). The reaction was stirred for about 6 hours. TLC showed the starting material was completely consumed. Then Pd/C was removed by filtration. The filtrate was concentrated. The residue was purified by column chromatography on silical gel to afford ethyl 3-(7-cyano-4-fluoro-1H-indol-3-yl)propanoate (D44) (6.0 g) as a white solid. δH (CDCl3, 400 MHz): 1.25 (3H, t), 2.72 (2H, t), 3.18 (2H, t), 4.14 (2H, q), 6.82 (1H, t), 7.10 (1H, s), 7.45 (1H, q), 8.88 (1H, s). MS (ES): C14H13FN2O2 requires 260; found 261.1 (M+H+).

Workup

  1. customwas completely consumed
  2. customThen Pd/C was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silical gel

Sources & evidence

ORD record
ord-8409099c7dec454fb0813f1c0c68a10a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…