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

HRID 428020

반응식

HRID 428020 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-733b89533ee64034b26e3ebb33f90f79
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313151B1

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