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Ethyl Acetate → 8-chloro-7-methoxy-4-(4-methoxy-benzyloxy)-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline

HRID 388676
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HRID 388676 반응식
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[H-].[Na+].Cl[C:13]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:20]2[C:15](=[C:16]([Cl:35])[C:17]([O:33][CH3:34])=[CH:18][CH:19]=2)[N:14]=1.CCOC(C)=O>CN(C=O)C>[Cl:35][C:16]1[C:17]([O:33][CH3:34])=[CH:18][CH:19]=[C:20]2[C:15]=1[N:14]=[C:13]([N:5]1[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]1)[CH:22]=[C:21]2[O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 18070343-(Trifluoromethyl)pyrazoleHCID 566051532,8-Dichloro-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline

생성물 1

HCID 566051548-chloro-7-methoxy-4-(4-methoxy-benzyloxy)-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline수율 51%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a stirred solution of compound 233a (821 mg, 1.1 eq.) in anhydrous DMF (20 mL) at 0° C. was added NaH (241 mg, 1.1 eq.) portionwise. After the reaction mixture was stirred for 1 hr at room temperature, compound 221d (2 g, 1 eq.) was added and the mixture was stirred at 90° C. for 16 hrs. After the reaction mixture was cooled to room temperature, EtOAc was added. The organic phase was washed with HCl (2.5 N), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (petroleum ether/DCM, 50/50) to give compound 234a as a white solid in 51% yield. MS (ESI, EI−) m/z=461.9 (MH−).

후처리

  1. stirringthe mixture was stirred at 90° C. for 16 hrs
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. washThe organic phase was washed with HCl (2.5 N)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by chromatography on silica gel (petroleum ether/DCM, 50/50)

출처 및 근거

ORD 기록
ord-18e5ad63ba624142a383aaf45a235808
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377962B2

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