Benzyl 2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylate → 2-[4-(2-Methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid

HRID 1514956Notes

Reaction equation

HRID 1514956 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23]([O:25]CC2C=CC=CC=2)=[O:24])[CH:17]=3)=[C:9]([CH3:33])[CH:8]=1)=[O:4]>[Pd].C(OCC)(=O)C.C(O)C>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH3:33])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23]([OH:25])=[O:24])[CH:17]=3)=[C:11]([CH3:13])[CH:12]=1)=[O:4]

Participants

4

Reactant 1

HCID 66965810Benzyl 2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylate

Product 1

HCID 669662052-[4-(2-Methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of benzyl 2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylate (950 mg, 2.16 mmol) and 10% palladium on carbon (95 mg) in 100 mL of ethyl acetate/ethanol (1:1) was stirred under a hydrogen balloon for 18 h. The mixture was filtered through Celite to remove catalyst, and the solvent removed under reduced pressure to leave 2-[4-(2-methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid. MS (m/z) 352.2 (M+1): Retention time=1.35 min (Method 10).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove catalyst
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a01c3b7dece44568b7f3084956595a79
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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