HCID 59146165, compound → HCID 59146094, compound

HRID 1512833Notes

Reaction equation

HRID 1512833 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([F:19])[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.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([F:19])[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 59146165HCID 59146165, compound

Product 1

HCID 59146094HCID 59146094, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl (2E)-3-(7-cyano-5-fluoro-1H-indol-3-yl)-2-propenoate (D134) (4 g) in THF (100 mL) was added Pd/C (0.8 g, with 1% water). The reaction was stirred under H2 (50 psi) atmosphere at 50° C. for about 4 hrs, TLC showed the material was completely consumed. Then Pd/C was removed by filtration, the filtrate was concentrated and washed with PE to afford ethyl 3-(7-cyano-5-fluoro-1H-indol-3-yl)propanoate (D135) (2.57 g) as a white solid. δH (CDCl3, 400 MHz): 1.25 (3H, t), 2.67 (2H, t), 3.05 (2H, t), 4.14 (2H, q), 7.20 (1H, s), 7.25 (1H, dd), 7.52 (1H, dd), 8.64 (1H, br); 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. washwashed with PE

Sources & evidence

ORD record
ord-d6f24c39f4744ff8a31a5ffcc030e784
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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