Ethyl Acetate → 1-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-5-ol

HRID 1983554노트

반응식

HRID 1983554 반응식
[CH2:1]([C:5]1[N:6]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[S:8][C:9]=1[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[C:18]([O:20]C)[CH:19]=[C:14]2[CH:13]=[CH:12]1)[CH2:2][CH2:3][CH3:4].C(OCC)(=O)C>ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][CH:23]=2)[S:8][C:9]=1[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[C:18]([OH:20])[CH:19]=[C:14]2[CH:13]=[CH:12]1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 8857Ethyl AcetateHCID 577130301-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-5-methoxy-1h-pyrrolo[2,3-b]pyridine

생성물 1

HCID 577130271-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-5-ol수율 113%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

850 mg 1-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-5-methoxy-1H-pyrrolo[2,3- b]pyridine was dissolved in 50 ml dichloromethane. At −78° C. 1.90 ml of a 1 molar solution of borontribromide in dichloromethane was added. The reaction mixture was allowed to warm up to room temperature. Then the reaction mixture was heated under reflux for additional two hours. 150 ml ethyl acetate were added and the mixture washed with 50 ml of a one molar solution of hydrochloric acid. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by RP-HPLC to provide 930 mg 1-[4-Butyl-2-(4-trifluoromethylphenyl)-thiazol-5-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-5-ol as a lyophilisate.

후처리

  1. customAt −78° C
  2. temperatureThen the reaction mixture was heated
  3. temperatureunder reflux for additional two hours
  4. washthe mixture washed with 50 ml of a one molar solution of hydrochloric acid
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-9401c5c5bc7e4578a6c2c1dfde89f85f
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541464B2

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