Sodium Chloride → HCID 90416413、化合物

HRID 633605ノート

反応式

HRID 633605 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[CH:13]=[CH:12][NH:11][C:7]2=[C:8]([Cl:10])[N:9]=1.I[CH3:15].[Cl-].[NH4+].[Cl-].[Na+]>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]2[CH:13]=[CH:12][N:11]([CH3:15])[C:7]2=[C:8]([Cl:10])[N:9]=1

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 467379065-Bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine

生成物 1

HCID 90416413HCID 90416413、化合物収率 112.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in oil, 1.45 g, 36.3 mmol) was added portionwise to a 0° C. solution of 5-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine (CAS 1198096-48-8) (4.2 g, 18.14 mmol) and tetrahydrofuran (42 mL). After 15 minutes at 0° C. iodomethane (1.7 mL, 27.2 mmol) was added. The reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for 2 hours. The reaction mixture was cooled to 0° C. and 30 mL saturated aqueous ammonium chloride solution was added, followed by addition of saturated aqueous sodium chloride. The mixture was extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to afford 5 g yellow solid. The crude product was purified by flash chromatography (silica gel, 2-20% ethyl acetate in heptanes) to provide 3.7 g (84%) of the title compound.

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9d4a8e7f2311467d988d4125aec7da6a
出典データセット
uspto-grants-2016_04
特許番号
US09321764B2

反応ノート

読み込み中…