Methyl 4-(Chlorosulfonyl)benzoate → HCID 58975223, compound

HRID 737011Notes

Reaction equation

HRID 737011 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1([F:22])[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9]1.[CH3:23][O:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>O1CCOCC1>[CH3:23][O:24][C:25](=[O:36])[C:26]1[CH:27]=[CH:28][C:29]([S:32]([N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]([CH:10]3[CH2:11][CH2:12][C:8]([F:7])([F:22])[CH2:9]3)=[CH:14]2)(=[O:33])=[O:34])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 23665647Potassium tert-butoxideHCID 58975063HCID 58975063, compound

Product 1

HCID 58975223HCID 58975223, compoundYield 223.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add potassium tertbutoxide (368 mg, 3.28 mmol, 1.1 eq) to a 3 ml dioxane solution of 3-(3,3-difluoro-cyclopentyl)-1H-indole (660 mg, 2.98 mmol, 1.0 eq) under N2. Stir solution for 5 minutes. Add 4-Chlorosulfonyl-benzoic acid methyl ester 117 mg, 0.497 mmol, 1.1 eq). Stir reaction for 4 hours at room temperature. Strip reaction of solvent and purify by silica gel chromatography to give 4-[3-(3,3-Difluoro-cyclopentyl)-indole-1-sulfonyl]-benzoic acid methyl ester (466 mg, 37% yield).

Workup

  1. customreaction for 4 hours at room temperature
  2. customStrip reaction of solvent
  3. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-a7e1b1ecd97e437683b36368abeb22de
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…