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

HRID 1983554ノート

反応式

HRID 1983554 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9401c5c5bc7e4578a6c2c1dfde89f85f
出典データセット
uspto-grants-2009_06
特許番号
US07541464B2

反応ノート

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