Dimethylformamide → HCID 54112325、化合物

HRID 1678134ノート

反応式

HRID 1678134 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7](C)[CH:8]=[O:9].[C:11]1([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH2:19][C:18]2=O)C=CC=CC=1.[OH-].[NH4+]>O.ClCCl.N1C=CC=CC=1>[CH3:11][N:17]([CH:18]=[C:19]1[C:20]2[C:6](=[N:22][CH:23]=[CH:24][CH:25]=2)[NH:7][C:8]1=[O:9])[CH3:21]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 149872061-Phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

生成物 1

HCID 54112325HCID 54112325、化合物収率 47.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
2.5 °C

実験手順

Phosphorous oxychloride (693 μL, 7.47 mmol) is added slowly to a stirred solution of dimethylformamide (714 μL) and dichloromethane (714 μL) cooled to 0-5° C. After 10 min, a solution of the above 1-phenyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (350 mg, 1.66 mmol), pyridine (357 μL) and dichloromethane (1.43 mL) is added and the reaction is stirred at room temperature for 24 hr. The reaction mixture is poured into water, the pH adjusted to 8 with ammonium hydroxide and extracted with dichloromethane (2×). The combined extract is dried, filtered and concentrated. The residue is purified by chromatography eluting with dichlormethane-2% methanol. Product containing fractions are combined and concentrated to afford 3-dimethylaminomethylene-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (211 mg, 47.9% yield).

後処理

  1. extractionextracted with dichloromethane (2×)
  2. extractionThe combined extract
  3. customis dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography
  7. washeluting with dichlormethane-2% methanol
  8. additionProduct containing fractions
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-df616151b4a6439eb20dc84a62eb1dc7
出典データセット
uspto-grants-2011_08
特許番号
US08008491B2

反応ノート

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