1,2-Dibromoethane → 6-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole

HRID 38084

반응식

HRID 38084 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]([SH:14])[NH:12][N:13]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29]Br>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]3[S:14][CH2:28][CH2:29][N:12]3[N:13]=2)[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178489941HCID 178489941, 화합물

생성물 1

HCID 674229736-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole수율 61.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-(3-Methoxy-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (630 mg, 2.22 mmol) was dissolved in dry DMF (22 mL) under nitrogen atmosphere. Solid potassium carbonate (1.5 g, 11.1 mmol, 5 eq) was added followed by 1,2-dibromoethane (0.192 mL, 2.22 mmol, 1 eq) and the suspension was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure, diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated to dryness to give 420 mg (61% over two steps) of crude 6-(3-methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazole which was used without further purification in the following step.

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-4c0ef89d3b0b41639c930e4c95a53739
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524707B2

연결된 노트

불러오는 중…