Sodium hydride → 3-(3-Bromo-6,7-dihydro-5H-[1]pyrindin-7-yl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

HRID 1742425ノート

反応式

HRID 1742425 の反応式
[H-].[Na+].[CH2:3]([C:5]1[NH:15][C:8]2=[N:9][C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH3:4].[Br:16][C:17]1[CH:18]=[N:19][C:20]2[CH:21](Cl)[CH2:22][CH2:23][C:24]=2[CH:25]=1.[Na+].[Br-]>O1CCOCC1>[Br:16][C:17]1[CH:18]=[N:19][C:20]2[CH:21]([N:15]3[C:8]4=[N:9][C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:7]4[N:6]=[C:5]3[CH2:3][CH3:4])[CH2:22][CH2:23][C:24]=2[CH:25]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 253881Sodium BromideHCID 678430763-bromo-7-chloro-6,7-dihydro-5H-cyclopenta[b]pyridineHCID 178437439HCID 178437439、化合物

生成物 1

HCID 678430723-(3-Bromo-6,7-dihydro-5H-[1]pyrindin-7-yl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine収率 13.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

To a solution of NaH, 60% in oil, (163 mg) in 3 mL of 1,4-dioxane was added 2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (1.1 gm) at room temperature and stirred for 30 minutes. Then 3-bromo-7-chloro-6,7-dihydro-5H-[1]pyrindine (500 mg, 2.15 mM) in 2 mL of 1,4-dioxane and anhydrous NaBr (442 mg) were added to the solution and the reaction was heated to 100° C. for 24 hours. The reaction was then cooled to room temperature, concentrated to dryness, and extracted into ethyl acetate from water. The organic layers were dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by chromatography on silica gel to yield 110 mg of product.

後処理

  1. temperatureThe reaction was then cooled to room temperature
  2. concentrationconcentrated to dryness
  3. extractionextracted into ethyl acetate from water
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-0ba5798fcf0c4766be13fff8fba00fe5
出典データセット
uspto-grants-1994_08
特許番号
US05338740

反応ノート

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