HCID 10252039, compound → 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid

HRID 1739590Notes

Reaction equation

HRID 1739590 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22]CC4C=CC=CC=4)=[O:21])[CH:18]=3)[NH:13][CH:12]=2)=[C:6]([O:30][CH3:31])[CH:5]=1>CN(C)C=O.C(O)=O.[Pd]>[CH3:31][O:30][C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:32])[CH:9]=[CH:8][C:7]=1[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=2)[NH:13][CH:12]=1

Participants

5

Reactant 1

HCID 10252039HCID 10252039, compound

Product 1

HCID 103372503-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acidYield 73%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[5-benzoxycarbonyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (3.46 grams, 8.06 mmol) in dimethylformamide (40 mL) and formic acid (2 mL) was added 10% palladium on carbon (1.5 grams). The resulting mixture was hydrogenated at 30 psi for 1.5 hours. The mixture was filtered through celite and the filtrate diluted with ethyl acetate. This solution was washed several times with 1 M hydrochloric acid (aq). The organics were then dried over magnesium sulfate and concentrated. Recrystallization from methylene chloride gave 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid (1.97 grams, 73% yield).

Workup

  1. filtrationThe mixture was filtered through celite
  2. additionthe filtrate diluted with ethyl acetate
  3. washThis solution was washed several times with 1 M hydrochloric acid (aq)
  4. dry with materialThe organics were then dried over magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-64322bc4749042dda6e38d1988468d9d
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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