Sodium hydride → HCID 59437208, 화합물

HRID 244424

반응식

HRID 244424 반응식
[F:1][C:2]([F:31])([F:30])[C:3]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[OH:4].[H-].[Na+].[H][H].[CH2:36]1[O:39][C@@H:37]1[CH3:38]>C1COCC1.O>[F:31][C:2]([F:30])([F:1])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:36][C@H:37]([OH:39])[CH3:38])[CH:6]=1)([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)[OH:4]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 579433222,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanolHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 59437208HCID 59437208, 화합물수율 47.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a room temperature solution of 100 mg (0.23 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanol in THF was added 20.0 mg (0.50 mmol) of 60% NaH in mineral oil. After hydrogen evolution ceased, 14.5 mg (0.25 mmol) of (R)-(+)-propylene oxide was added. The reaction was then warmed at 60° C. for 5 hours. The reaction was then cooled to room temperature and diluted with water and extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (20-40% ethyl acetate in hexanes). The major fractions were combined and concentrated to provide 53 mg (46.6%) of the title compound. MS m/z 484.47 (MH+).

후처리

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted with ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (20-40% ethyl acetate in hexanes)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d38917c0815b4762a6161b1dc61302f2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

연결된 노트

불러오는 중…