Methyl iodide → 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

HRID 2208991ノート

反応式

HRID 2208991 の反応式
IC.[Cl:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[C:7]2[NH:12][CH:13]=[N:14][C:6]=2[CH:5]=1.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[C:7]2[N:12]([CH3:15])[CH:13]=[N:14][C:6]=2[CH:5]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178503471HCID 178503471、化合物

生成物 1

HCID 1178434146-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Iodomethane (0.52 mL, 8.36 mmol) was added to a solution of 6-chloro-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.01 (1.40 g, 7.04 mmol) and potassium carbonate (1.95 g, 14.1 mmol) in 46 mL of DMF at room temperature. After 90 minutes, reaction mixture was taken up in ethyl acetate (150 mL) and washed with 50% saturated NaHCO3 (aq)(2×100 mL). After separating layers, aqueous was extracted with ethyl acetate (100 mL). All combined organic layers were washed with 50% brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield a solid. This was purified via silica gel column chromatography (5-25% acetone in hexanes) to yield 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.02 (first eluting product).

後処理

  1. customreaction mixture
  2. washwashed with 50% saturated NaHCO3 (aq)(2×100 mL)
  3. customAfter separating layers
  4. extractionaqueous was extracted with ethyl acetate (100 mL)
  5. washAll combined organic layers were washed with 50% brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a solid
  10. customThis was purified via silica gel column chromatography (5-25% acetone in hexanes)

出典と根拠

ORDレコード
ord-eec70d70a8e44b0890ce52dfc84852a6
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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