Dimethylformamide → HCID 86035948、化合物

HRID 1678126ノート

反応式

HRID 1678126 の反応式
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[S:11]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C:17]2=O)=[CH:12]1>ClCCl.N1C=CC=CC=1>[Cl:3][C:17]1[N:16]([C:13]2[CH:14]=[CH:15][S:11][CH:12]=2)[C:24]2[C:19]([C:18]=1[CH:8]=[O:9])=[CH:20][CH:21]=[CH:22][CH:23]=2

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 148193781-(Thiophen-3-yl)-1,3-dihydro-2H-indol-2-one

生成物 1

HCID 86035948HCID 86035948、化合物収率 57%

試薬・触媒・溶媒 2

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 (1.9 mL, 20.9 mmol) is added slowly to a stirred solution of dimethylformamide (2 mL) and dichloromethane (2 mL) cooled to 0-5° C. After 5 min, a solution of the above 1-(thien-3-yl)-1H-indol-2-one (1.0 g, 2.65 mmol), pyridine (1 mL) and dichloromethane (4 mL) is added and the reaction is stirred at room temperature for 48 hr. The reaction mixture is poured into ice/water and extracted with ethyl acetate. Some solids are removed by filtration and the organic layer is separated, dried, filtered and concentrated. The residue is purified by chromatography eluting with pentane-10% ethyl acetate. Product containing fraction are combined and concentrated to afford 2-chloro-1-(thien-3-yl)-1H-indole-3-carboxaldehyde (694 mg, 57%) as a light orange solid. MS 262 (M+H).

後処理

  1. extractionextracted with ethyl acetate
  2. customSome solids are removed by filtration
  3. customthe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography
  8. washeluting with pentane-10% ethyl acetate
  9. additionProduct containing fraction
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-b866101aaf18450d83c5c75dfcad1907
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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