4-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazole → 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

HRID 216394ノート

反応式

HRID 216394 の反応式
C([Li])CCC.[CH3:6][C:7]([CH3:36])([CH2:34][CH3:35])[CH2:8][C:9]1[N:10]=[C:11]([CH3:33])[N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1.[F:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]2[CH:55]=[CH:54][C:47]([C:48](N(OC)C)=[O:49])=[CH:46][CH:45]=2)=[N:42][CH:43]=1>O1CCCC1>[CH3:6][C:7]([CH3:36])([CH2:34][CH3:35])[CH2:8][C:9]1[N:10]=[C:11]([CH2:33][C:48]([C:47]2[CH:46]=[CH:45][C:44]([C:41]3[CH:40]=[CH:39][C:38]([F:37])=[CH:43][N:42]=3)=[CH:55][CH:54]=2)=[O:49])[N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1

参加物

5

反応物 3

HCID 591619684-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazoleHCID 866384894-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 686681262-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

n-Butyllithium (2.5 M in hexanes) (0.53 mL, 1.32 mmol) was added to a solution of 4-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazole (360 mg, 0.88 mmol) in tetrahydrofuran (15 mL) at −78° C. dropwise. After stirring at −78° C. for 40 min, 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide (340 mg, 1.32 mmol) in tetrahydrofuran (5 mL) was added dropwise. After warming slowly to ambient temperature, the reaction mixture was quenched with saturated aqueous ammonium chloride. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone contaminated with an unidentified byproduct. This material was used in the next step without further purification.

後処理

  1. temperatureAfter warming slowly to ambient temperature
  2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-96d46e947a1c423bbd0e6f2aaff59578
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

反応ノート

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