Water → [2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-carbamic acid tert-butyl ester

HRID 1051215노트

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HRID 1051215 반응식
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]2[C:17]([O:23][CH3:24])=[N:18][CH:19]=[CH:20][C:21]=2[Cl:22])=[C:10]([N+:25]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O>P(OCC)(OCC)OCC>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:9]=[C:10]2[C:11]([CH:14]=[C:15]([C:16]3[C:17]([O:23][CH3:24])=[N:18][CH:19]=[CH:20][C:21]=3[Cl:22])[NH:25]2)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 962WaterHCID 90102932{4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

생성물 1

HCID 90102920[2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-carbamic acid tert-butyl ester수율 33%

시약·촉매·용매 1

HCID 31215Triethyl phosphite용매

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온도
25 °C

실험 절차

A solution of {4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (800 mg, 1.97 mmol) in triethyl phosphite (16.0 ml) was refluxed for 3 hours. The reaction mixture was cooled to 25° C., and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded [2-(4-chloro-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-carbamic acid tert-butyl ester (180 mg, 33%) as a white solid. MH+ 374.0.

후처리

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo
  6. customgave a brown solid

출처 및 근거

ORD 기록
ord-173a6a15a00f414892a11a05646dfef6
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388166B2

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