Methyl iodide → 6-Fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine

HRID 245873ノート

反応式

HRID 245873 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[S:11])[NH:9][CH:10]=2)[CH:7]=1.[CH3:12][O-].[Na+].CI>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 866779106-fluoro-2H-imidazo[1,5-a]pyridine-3-thione

生成物 1

HCID 866779116-Fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine収率 104.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In a round-bottomed flask, 6-fluoro-2H-imidazo[1,5-a]pyridine-3-thione (158 mg, 0.94 mmol) was suspended in methanol (1 ml) and sodium methoxide (0.5 M in MeOH, 2.0 ml, 1.0 mmol) was added dropwise. The reaction was stirred at room temperature for 10 min then methyl iodide (0.07 ml, 1.12 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane then the organic layers were combined, dried over sodium sulfate, filtered and concentrated to afford 179 mg of 6-fluoro-3-methylsulfanyl-imidazo[1,5-a]pyridine as a brown oil which was used without further purification. 1H NMR (CDCl3, 400 MHz): δ (ppm) 7.98-8.05 (m, 1H), 7.58 (s, 1H), 7.45 (dd, J=9.3, 4.8 Hz, 1H), 6.73 (ddd, J=9.6, 7.6, 2.0 Hz, 1H), 2.56 (s, 3H).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. concentrationthen concentrated
  3. customThe residue was partitioned between dichloromethane and water
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-22587c21dd7b492cae8ef59cc5220728
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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