Sodium Carbonate → (E)-4-(Hex-3-en-3-yl)-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 1698533노트

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HRID 1698533 반응식
Br[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:19][CH2:20]/[C:21](/B1OC2C=CC=CC=2O1)=[CH:22]\[CH2:23][CH3:24]>C1(C)C=CC=CC=1>[CH3:19][CH2:20]/[C:21](/[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1)=[CH:22]\[CH2:23][CH3:24]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 65339122-[(Z)-hex-3-en-3-yl]-1,3,2-benzodioxaboroleHCID 866371924-Bromo-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

생성물 1

HCID 67272545(E)-4-(Hex-3-en-3-yl)-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one수율 58%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
90 °C

실험 절차

A mixture of 0.68 g (3.0 mmol) of 4-bromo-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one and 0.17 g (0.20 mmol) of PdCl2dppf-dichloromethane complex was dissolved in 12 mL of toluene and treated with 3.8 mL (7.7 mmol) of 2N sodium carbonate and 0.72 g (3.6 mmol) of (Z)-2-(hex-3-en-3-yl)benzo[d][1,3,2]dioxaborole. The resulting mixture was heated to 90° C. for 5 h, partitioned between water and ethyl acetate, filtered to remove fine precipitates and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The brown oil thus obtained was purified by flash chromatography eluting with a 25% methanol/dichloromethane mixture to give 0.40 g (58%) of the title compound as a cream colored solid.

후처리

  1. custompartitioned between water and ethyl acetate
  2. filtrationfiltered
  3. customto remove fine
  4. customprecipitates
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe brown oil thus obtained
  11. customwas purified by flash chromatography
  12. washeluting with a 25% methanol/dichloromethane mixture

출처 및 근거

ORD 기록
ord-d20a50eece114294bf539eb6801bde7f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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