Boron tribromide → 3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenol

HRID 38101노트

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HRID 38101 반응식
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:12]3[S:13][CH:14]=[CH:15][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:20]1[CH:19]=[CH:18][C:17]([C:16]2[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)=[N:10][N:11]3[CH:15]=[CH:14][S:13][C:12]=23)=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 674234366-(3-Methoxy-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole

생성물 1

HCID 467019743-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenol수율 80.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

6-(3-Methoxy-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole (65 mg, 0.212 mmol) was dissolved in dry DCM (2 mL) and cooled to 0° C. A 1 M solution of boron tribromide in DCM (0.850 mL, 0.848 mmol, 4 eq) was added dropwise and the mixture was allowed to warm to room temperature and stirred for 1 hours. Ice was then added to the reaction mixture, followed by saturated aqueous NaHCO3 until pH 6. The aqueous phase was extracted with DCM and the organic layer was dried and evaporated to dryness. An insoluble solid formed during extraction and it was filtered and combined with the organic layer. The crude product was taken up with toluene and concentrated to dryness three times and the same treatment was repeated with DCM. 50 mg of 3-(7-pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenol (80%) were obtained as pale yellow solid.

후처리

  1. temperatureto warm to room temperature
  2. additionIce was then added to the reaction mixture
  3. extractionThe aqueous phase was extracted with DCM
  4. customthe organic layer was dried
  5. customevaporated to dryness
  6. customAn insoluble solid formed during extraction and it
  7. filtrationwas filtered
  8. concentrationconcentrated to dryness three times

출처 및 근거

ORD 기록
ord-09b308db305d4ac3808ac399b8414822
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524707B2

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