Triethyl phosphonoacetate → Ethyl 2-(7-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate

HRID 1964149노트

반응식

HRID 1964149 반응식
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=O)[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32].[NH4+].[Cl-]>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32]

참가 물질

6

반응물 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672497037-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one

생성물 1

HCID 67249397Ethyl 2-(7-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate수율 54.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (1.38 mL, 6.97 mmol) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil) (279 mg, 6.97 mmol) at 0° C. The reaction mixture was stirred for 10 min, then 7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (500 mg, 2.323 mmol) in DMF (6 mL) was added. The reaction mixture was warmed to room temperature and stirred for 1 h, then heated at 60° C. for 1 h, cooled down, poured into saturated NH4Cl aqueous solution, extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (361 mg). LCMS m/z=286.2 [M+H]+.

후처리

  1. stirringstirred for 1 h
  2. temperatureheated at 60° C. for 1 h
  3. temperaturecooled down
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9ee92a99de4b40b0883976016f894de9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415484B2

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