Ethyl Acetate → 4-(3-Cyano-6-hydroxyindol-1-yl)-2-methoxymethoxybenzoic acid ethyl ester

HRID 1258210Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20]CC4C=CC=CC=4)[CH:18]=3)[C:13]([C:28]#[N:29])=[CH:12]2)=[CH:7][C:6]=1[O:30][CH2:31][O:32][CH3:33])[CH3:2].C(OCC)(=O)C>[C].[Pd].CO>[CH2:1]([O:3][C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=3)[C:13]([C:28]#[N:29])=[CH:12]2)=[CH:7][C:6]=1[O:30][CH2:31][O:32][CH3:33])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(6-benzyloxy-3-cyanoindol-1-yl)-2-methoxymethoxybenzoic acid ethyl ester in a mixed solvent of ethyl acetate (60 mL) and methanol (60 mL) was added palladium-carbon powder (0.61 g) under 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 to give the title compound (2.5 g)

Workup

customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-fcdd4930141d491f8475d74c0450cba8
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466152B2

Reaction notes

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