Potassium Carbonate → 6-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl Ester

HRID 988258노트

반응식

HRID 988258 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2C)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([O:1][C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH3:13])([CH3:14])[C:7](=[O:12])[NH:8]3)=[CH:4][CH:3]=2)[CH3:32])[CH:24]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-oneHCID 542191176-(3-Bromomethyl-phenyl)-hexanoic Acid Methyl Ester

생성물 1

HCID 692161446-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl Ester수율 41.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of 6-hydroxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (396 mg, 2.07 mmol) in DMF (7.6 mL) is added 6-(3-Bromomethyl-phenyl)-hexanoic acid methyl ester (682 mg, 2.28 mmol) and potassium carbonate (315 mg, 2.28 mmol). The resulting mixture is heated to 60° C., stirred for 2 hrs. then cooled to room temp and diluted with EtOAc. The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes) to give 352 mg of title compound. MS (ESI) 410 (M+H)+.

후처리

  1. temperaturethen cooled to room temp
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-41a6895f53ba4afea93c2989834d5a19
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635655B1

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