Sodium hydride → Methyl 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate

HRID 332083

반응식

HRID 332083 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[H-].[Na+].[C:18]([O:23][CH3:24])(=[O:22])[CH:19]1[O:21][CH2:20]1>CN(C=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:20][CH:19]([OH:21])[C:18]([O:23][CH3:24])=[O:22])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 145751Methyl oxirane-2-carboxylateHCID 2748743,6-Dibromocarbazole

생성물 1

HCID 58097196Methyl 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

3,6-Dibromocarbazole (0.300 g, 0.923 mmol) was dissolved in DMF (1.2 mL) and cooled to 0° C. NaH (60% dispersion in mineral oil, 0.074 g, 1.846 mmol) was added and the reaction stirred for 1 h at 0° C. Methyl glycidate (0.471 g, 4.615 mmol) was added and the reaction was stirred and warmed to ambient temperature over 3.5 h. Upon completion by TLC the reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted 3× with EtOAc, and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane) to afford the desired product (125 mg, 32%).

후처리

  1. stirringthe reaction was stirred
  2. temperaturewarmed to ambient temperature over 3.5 h
  3. customUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
  4. extractionThe aqueous layer was extracted 3× with EtOAc
  5. washthe combined organics were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-c1bb16421612404497c2e8067e7b412a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877797B2

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