Dichloromethane → [3-(2-Chlorosulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

HRID 1944426ノート

反応式

HRID 1944426 の反応式
[CH3:1][O:2][C:3](=[O:27])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22](O)(=[O:24])=[O:23])=[C:6]1[CH3:26].[Cl:28]CCl.P(Cl)(Cl)(Cl)(Cl)Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22]([Cl:28])(=[O:24])=[O:23])=[C:6]1[CH3:26]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 86652190[5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester

生成物 1

HCID 86652191[3-(2-Chlorosulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of [5-fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester (0.30 g) and dichloromethane (1.5 mL) was treated portion wise with phosphorus pentachloride (0.15 g), followed by N,N-dimethylformamide (0.070 mL), and the resulting mixture was heated at reflux overnight. The mixture was cooled to room temperature, concentrated under reduced pressure and diluted with dichloromethane. The mixture was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane to afford the title compound as a yellow solid (1.3 g).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with dichloromethane
  5. washThe mixture was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-fd5e5e477a7b409c985fdf317bfb0237
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

反応ノート

読み込み中…