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

HRID 1698533ノート

反応式

HRID 1698533 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d20a50eece114294bf539eb6801bde7f
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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