Sodium Carbonate → N-(3-Chloro-6-trifluoromethylimidazo[1,2-a]pyridin-2-yl)-N-(3-fluoro-4-trifluoromethylbenzyl)benzenesulfonamide

HRID 1916858Notes

Reaction equation

HRID 1916858 reaction equation
[Cl:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17].C([O-])([O-])=O.[Na+].[Na+].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[C:40]([F:43])([F:42])[F:41])[CH2:35]Br>CN(C=O)C>[Cl:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]([F:12])([F:14])[F:13])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[N:15]([CH2:35][C:34]1[CH:37]=[CH:38][C:39]([C:40]([F:41])([F:42])[F:43])=[C:32]([F:31])[CH:33]=1)[S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27375744-(Bromomethyl)-2-fluoro-1-(trifluoromethyl)benzeneHCID 67953932N-(3-chloro-6-trifluoromethylimidazo[1,2-a]pyridin-2-yl)benzenesulfonamide

Product 1

HCID 88531008N-(3-Chloro-6-trifluoromethylimidazo[1,2-a]pyridin-2-yl)-N-(3-fluoro-4-trifluoromethylbenzyl)benzenesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 9-E (0.015 g, 0.025 mmol) in DMF (2.0 mL) was added Na2CO3 (0.011 g, 0.099 mmol) and 3-fluoro-4-trifluoromethylbenzyl bromide (0.006 g, 0.025 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2) eluting with a gradient of 0-100% ethyl acetate in hexane to afford Compound 60 (0.008 g, 58%); MS m/z (M+H+) 552.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2)
  3. washeluting with a gradient of 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ec5564d457b9429794b3381fe1bcdc23
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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