1-Bromo-3-chloropropane → 6-(3-Chloropropoxy)-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole

HRID 1897472

반응식

HRID 1897472 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][CH2:32][CH2:33][Cl:34]>CN(C=O)C.O.CCOCC>[Cl:34][CH2:33][CH2:32][CH2:31][O:14][C:13]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:6][C:5]=1[O:4][C:3]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:2]=1[F:1]

참가 물질

7

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 1361636625-(2,4-difluorophenoxy)-1-isobutyl-1H-indazol-6-ol

생성물 1

HCID 674106266-(3-Chloropropoxy)-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazol-6-ol (0.015 g, 0.05 mmol) in DMF (1 mL) was added Cs2CO3. The reaction mixture was stirred for 30 minutes before the addition of 1-bromo-3-chloropropane (0.01 g, 0.08 mmol) and then was heated to 80° C. for 25 hours. After cooling the mixture to room temperature, the reaction mixture was diluted with water and ether and the layers separated. The aqueous layer was extracted with ether and the combined organic layers were washed with 1N NaOH, water, and brine. The crude mixture was dried over Na2SO4 and concentrated under reduced pressure to afford the product with a small impurity. The crude mixture was used in the next reaction without further purification.

후처리

  1. temperatureAfter cooling the mixture to room temperature
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with ether
  4. washthe combined organic layers were washed with 1N NaOH, water, and brine
  5. dry with materialThe crude mixture was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the product with a small impurity

출처 및 근거

ORD 기록
ord-fffee2b82dfd42d9b41cf7503a029eb1
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518983B2

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