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

HRID 852265ノート

反応式

HRID 852265 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9a7b884eb5524f92ac7cc931af8e1fc3
出典データセット
uspto-grants-2007_08
特許番号
US07253183B2

反応ノート

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