Ethyl Acetate → HCID 25052342, compound

HRID 73357Notes

Reaction equation

HRID 73357 reaction equation
C(OC([NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:34]#[N:35])=[CH:20][N:21]2[C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[C:26]([OH:33])[CH:25]=2)=[CH:17][CH:16]=1)=O)C1C=CC=CC=1.C(OCC)(=O)C>[C].[Pd].CO>[NH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:34]#[N:35])=[CH:20][N:21]2[C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[C:26]([OH:33])[CH:25]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 250521884-[6-(2-Benzyloxycarbonylaminoethyloxy)-3-cyanoindol-1-yl]-2-hydroxybenzoic acid

Product 1

HCID 25052342HCID 25052342, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-[6-(2-benzyloxycarbonylaminoethyloxy)-3-cyanoindol-1-yl]-2-hydroxybenzoic acid (0.087 g) in a mixed solvent ethyl acetate (2 mL) and methanol (2 mL) was added palladium-carbon powder (0.016 g) under an argon atmosphere at 0° C., and this mixture was stirred at 40° C. under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. This obtained light yellow solid was washed with diethyl ether, dried to give the title compound (0.058 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThis obtained light yellow solid was washed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-ece489080e124efe86c8db7c127653eb
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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