p-Anisoyl chloride → Ethyl 3-(4-methoxybenzamido)-1H-indole-2-carboxylate

HRID 1370654Notes

Reaction equation

HRID 1370654 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH2:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N(CC)CC)C.[C:23](Cl)(=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Product 1

HCID 751363Ethyl 3-(4-methoxybenzamido)-1H-indole-2-carboxylateYield 94.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-2-indolecarboxylic acid ethyl ester (500 mg, 2.45 mmol) and triethylamine (272 mg, 2.70 mmol) in methylene chloride (5 mL) was added anisoyl chloride (418 mg, 2.45 mmol). The resulting mixture was stirred for 18 h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was washed with 1 N aqueous hydrochloric acid, dried (sodium sulfate), filtered, and concentrated in vacuo to provide a yellow solid. Recrystallization from hexane/ethyl acetate provided 780 mg (94%) of the title compound as a yellow solid.

Workup

  1. washwashed with water
  2. washThe organic phase was washed with 1 N aqueous hydrochloric acid
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a yellow solid
  7. customRecrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-7a7d13eaf1bd45bfaefc67da90b1fdd7
Source dataset
uspto-grants-2003_06
Patent number
US06583173B2

Reaction notes

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