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

HRID 1944426Notes

Reaction equation

HRID 1944426 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fd5e5e477a7b409c985fdf317bfb0237
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

Loading…