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 1742425노트

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HRID 1742425 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ba5798fcf0c4766be13fff8fba00fe5
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338740

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