Cesium carbonate → 5-(2,4-Difluorophenoxy)-1-isobutyl-6-oxiranylmethoxy-1H-indazole

HRID 909194

반응식

HRID 909194 반응식
[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[OH:14])[N:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:9]=[CH:8]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][CH:32]1[CH2:34][O:33]1>CC(N(C)C)=O.CCOCC.O>[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH2:31][CH:32]1[CH2:34][O:33]1)[N:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:9]=[CH:8]2

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 1361636625-(2,4-difluorophenoxy)-1-isobutyl-1H-indazol-6-ol

생성물 1

HCID 865944235-(2,4-Difluorophenoxy)-1-isobutyl-6-oxiranylmethoxy-1H-indazole수율 77%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazol-6-ol (0.15 g, 0.47 mmol) in DMA (5 mL) was added Cs2CO3 (0.46 g, 1.41 mmol). After stirring the mixture for 3 hours, 2-bromomethyloxirane (0.13 g, 0.94 mmol) was added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was diluted with ether and water and the layers were separated. The aqueous layer was extracted with ether (3×) and the combined organic layers were washed with water and brine, and dried over Na2SO4. The crude product was concentrated under reduced pressure and used in the next reaction without further purification (0.135 g, 77% yield).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ether (3×)
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe crude product was concentrated under reduced pressure
  7. customused in the next reaction without further purification (0.135 g, 77% yield)

출처 및 근거

ORD 기록
ord-087766101ac54eff8edeac4b5f2ab924
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017641B2

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