Potassium Carbonate → 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorobenzenesulfonamide

HRID 1627271Notes

Reaction equation

HRID 1627271 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([SH:23])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25].Br[CH2:27][C:28]1[C:33]([F:34])=[CH:32][C:31]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:30][C:29]=1[F:39].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:27][C:28]3[C:33]([F:34])=[CH:32][C:31]([S:35]([NH2:38])(=[O:36])=[O:37])=[CH:30][C:29]=3[F:39])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 667398554-(Bromomethyl)-3,5-difluorobenzenesulfonamideHCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

Product 1

HCID 469094314-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorobenzenesulfonamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (170 mg, 0.45 mmol, 1.0 eq), 4-(bromomethyl)-3,5-difluorobenzenesulfonamide (155 mg, 0.54 mmol, 1.2 eq) and K2CO3 (94 mg, 0.68 mmol, 1.5 eq) in acetone (2.3 mL) was stirred for 30 min. The reaction mixture was filtered, and the filtrate was concentrated and purified (silica, 0-75% EtOAc/Hex) to afford the title compound (252 mg, 96%) as a white solid. MS (EI) m/z 584 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified (silica, 0-75% EtOAc/Hex)

Sources & evidence

ORD record
ord-bcb982535f5b494eb2f18b70d7680b4c
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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