Chlorosulfonic acid → ethyl 2-(3-(2-(chlorosulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetate

HRID 1919851Notes

Reaction equation

HRID 1919851 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([O-])(=[O:25])=[O:24])=[C:7]1[CH3:27])[CH3:2].[Na+].[Cl:30]S(O)(=O)=O>>[Cl:30][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:28])[C:7]=1[CH3:27])(=[O:25])=[O:24]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86633021HCID 86633021, compound

Product 1

HCID 86633020ethyl 2-(3-(2-(chlorosulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetateYield 89%

Procedure

Sodium 2-((1-(2-ethoxy-2-oxoethyl)-5-fluoro-2-methyl-1H-indol-3-yl)methyl)benzenesulfonate (2.30 g, 5.38 mmol) was added portionwise to chlorosulfonic acid (10 ml) at room temperature (20° C.) over 20 min. The resulting mixture was stirred at room temperature for 2 hours, then poured onto ice/water (300 mL). The solution was next extracted with CH2Cl2, and the separated organics washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford ethyl 2-(3-(2-(chlorosulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetate (2.03 g, 4.79 mmol, 89%), which was used in the next step without further purification.

Workup

  1. additionpoured onto ice/water (300 mL)
  2. extractionnext extracted with CH2Cl2
  3. washthe separated organics washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-682d6d3890b947a681dc4064c5d793d7
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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