1-Carbamoyl-1H-indole-3-carboxylic acid benzyl ester → 1-carbamoyl-1H-indole-3-carboxylic acid

HRID 1052096Notes

Reaction equation

HRID 1052096 reaction equation
C([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20](=[O:22])[NH2:21])[CH:12]=1)=[O:10])C1C=CC=CC=1>CN(C=O)C.C1COCC1.CCOCC.[Pd]>[C:20]([N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:9]([OH:10])=[O:8])=[CH:12]1)(=[O:22])[NH2:21]

Participants

5

Reactant 1

HCID 682844691-Carbamoyl-1H-indole-3-carboxylic acid benzyl ester

Product 1

HCID 682835371-carbamoyl-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

1-Carbamoyl-1H-indole-3-carboxylic acid benzyl ester (1.33 g, 4.52 mmol) was dissolved in a mixture of DMF/THF 1:1 (28 mL), Pd/C (10%, 250 mg) was added and the solution was degassed 3 times replacing air with nitrogen then nitrogen with hydrogen. The reaction mixture was further stirred under hydrogen atmosphere overnight and the catalyst was removed through a pad of Celite and washed with THF. The solvents were concentrated under high vacuum to give a yellow solid which was taken up in Et2O and filtered-off to afford the title compound. 1H-NMR (400 MHz, DMSO): δ (ppm) 12.6 (m, 1H), 8.54 (bs, 1H), 8.28 (d, 1H), 8.05 (d, 1H), 7.85 (m, 2H), 7.34-7.27 (m, 2H).

Workup

  1. additionwas added
  2. customthe solution was degassed 3 times
  3. customthe catalyst was removed through a pad of Celite
  4. washwashed with THF
  5. concentrationThe solvents were concentrated under high vacuum
  6. customto give a yellow solid which

Sources & evidence

ORD record
ord-4cda0a487e414c2eb3656b163c607f5d
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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