Sodium hydride → 4-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole

HRID 2277498ノート

反応式

HRID 2277498 の反応式
[Br:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].Br[CH2:10][CH2:11][O:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.O>[Br:1][C:2]1[N:6]=[CH:5][N:4]([CH2:10][CH2:11][O:12][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:3]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 961251H-Imidazole, 4-bromo-HCID 109595312-Bromoethyl trityl ether

生成物 1

HCID 693507044-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole収率 69%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 5-bromo-1H-imidazole as prepared in part A (2.2 g, 15 mmol) in DMF (22 mL) at 0° C. was added NaH (658 mg, 60% dispersion, 2.42 mmol) in small portions. The resulting solution was allowed to warm to r.t. and then stirred for 1 hr. The solution was cooled to 0° C. and 1,1′,1″-[(2-bromoethoxy)methanetriyl]tribenzene (5.5 g, 15 mmol) in DMF (10 mL) was added drop-wise. The resulting solution was allowed to warm to r.t. where stirring continued until the reaction was judged complete by TLC (16 hr). The suspension was diluted with water and extracted with DCM (2×50 mL). The organics were dried (MgSO4), filtered, and concentrated to a solid that was recrystallized (EtOAc/Hex) to give 4.47 g of the title compound (69%).

後処理

  1. temperatureThe solution was cooled to 0° C.
  2. temperatureto warm to r.t. where
  3. stirringstirring
  4. customwas judged complete by TLC (16 hr)
  5. extractionextracted with DCM (2×50 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customthat was recrystallized (EtOAc/Hex)

出典と根拠

ORDレコード
ord-0d07b7590e494ced8a0450ef71f6a459
出典データセット
uspto-grants-2015_09
特許番号
US09133166B2

反応ノート

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