Water → (+/-)-alpha-(1-butyl-1H-imidazol-5-yl)-4-(3-chlorophenyl)-alpha-(4-chlorophenyl)-2-methoxy-6-quinolinemethanol

HRID 351775노트

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HRID 351775 반응식
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[C:10]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1.[CH2:26]([N:30]1[C:34]([C:35]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)=[O:36])=[CH:33][N:32]=[CH:31]1)[CH2:27][CH2:28][CH3:29].O>CCCCCC.C1COCC1>[CH2:26]([N:30]1[C:34]([C:35]([C:37]2[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=2)([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[C:10]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[OH:36])=[CH:33][N:32]=[CH:31]1)[CH2:27][CH2:28][CH3:29]

참가 물질

7

반응물 4

HCID 962WaterHCID 120166726-Bromo-4-(3-chlorophenyl)-2-methoxyquinolineHCID 22714358(1-butyl-1H-imidazol-5-yl)(4-chlorophenyl)methanoneHCID 178418339Butyllithium

생성물 1

HCID 22714345(+/-)-alpha-(1-butyl-1H-imidazol-5-yl)-4-(3-chlorophenyl)-alpha-(4-chlorophenyl)-2-methoxy-6-quinolinemethanol수율 48%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
-20 °C

실험 절차

Butyllithium in hexane (1.6 M) (12.75 ml) was added dropwise at −20° C. under N2 to a solution of 6-bromo-4-(3-chlorophenyl)-2-methoxyquinoline (6.7 g) in THF (60 ml) and the mixture was stirred at −20° C. for 30 minutes. A solution of (1-butyl-1H-imidazol-5-yl)(4-chlorophenyl)methanone (3.35 g) in tetrahydrofuran (30 ml) was added at −20° C. under N2 and the mixture was stirred at room temperature for one night. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1). The pure fractions were collected and evaporated, yielding 2.5 g (total 48%) of (±)-α-(1-butyl-1H-imidazol-5-yl)-4-(3-chlorophenyl)-a-(4-chlorophenyl)-2-methoxy-6-quinoline-methanol (interm. 2).

후처리

  1. stirringthe mixture was stirred at room temperature for one night
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1)
  7. customThe pure fractions were collected
  8. customevaporated

출처 및 근거

ORD 기록
ord-576dad662c8247b2b363c696b3073c3c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743805B2

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