Chlorosulfonic acid → HCID 86633024, compound

HRID 1919870Notes

Reaction equation

HRID 1919870 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([O:8][C:9](=[O:29])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=2)[C:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:12]1[CH3:28])[CH3:7]>>[CH2:6]([O:8][C:9](=[O:29])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=2)[C:13]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:26][CH:27]=2)=[C:12]1[CH3:28])[CH3:7]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 44198540HCID 44198540, compound

Product 1

HCID 86633024HCID 86633024, compoundYield 94%

Procedure

To chlorosulfonic acid (1.5 mL) at 0° C. under nitrogen was added portionwise over 10 minutes 2-(3-benzyl-5-fluoro-2-methyl-1H-indol-1-yl)acetic acid ethyl ester (900 mg, 2.76 mmol). After stirring at this temperature for 2 hours the solution was warmed to room temperature and stirred for a further 2 hours. The reaction mixture was then poured onto ice, and extracted with ethyl acetate. The separated organics were dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give 2-(3-(4-(chlorosulfonyl)benzyl)-5-fluoro-2-methyl-1H-indol-1-yl)acetic acid ethyl ester (˜1.1 g, 2.59 mmol, 94%) as a brown oil, which was used directly without further purification.

Workup

  1. stirringstirred for a further 2 hours
  2. additionThe reaction mixture was then poured onto ice
  3. extractionextracted with ethyl acetate
  4. dry with materialThe separated organics were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f7db0f23e294648a7991074ac2bc439
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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