HCID 68283626, compound → HCID 68283590, compound

HRID 1527162Notes

Reaction equation

HRID 1527162 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:23])[NH:21][CH3:22])[CH:12]=1)=[O:10])C1C=CC=CC=1>CO.C(Cl)Cl.[Pd]>[CH3:22][NH:21][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:23]

Participants

4

Reactant 1

HCID 68283626HCID 68283626, compound

Product 1

HCID 68283590HCID 68283590, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

To 1-Methylcarbamoyl-1H-indole-3-carboxylic acid benzyl ester (115 mg, 0.373 mmol) dissolved in a mixture of MeOH/CH2Cl2 1-1 (4 mL), Pd/C 10% (20 mg) was added and the solution was degassed 3 times replacing air by nitrogen and finally nitrogen by hydrogen. The reaction mixture was further stirred under hydrogen atmosphere for 1 h. The mixture was placed under a nitrogen atmosphere and the catalyst was removed through a pad of Celite and washed with MeOH. Solvents were concentrated under vacuum to give the desired compound. MS (LC/MS): 219.1 [M+H]+; tR (HPLC conditions a): 2.54 min.

Workup

  1. additionwas added
  2. customthe solution was degassed 3 times
  3. customthe catalyst was removed through a pad of Celite
  4. washwashed with MeOH
  5. concentrationSolvents were concentrated under vacuum

Sources & evidence

ORD record
ord-061780ffceda49dba498aaafccc9592b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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