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

HRID 83913Notes

Reaction equation

HRID 83913 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].C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]1[C:35]([Cl:45])=[CH:36][C:37]([F:44])=[C:38]([S:40]([NH2:43])(=[O:42])=[O:41])[CH:39]=1>CC(C)=O>[Cl:45][C:35]1[C:34]([CH2:33][S:23][C:14]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:24][CH3:25])[CH:4]=3)([CH3:10])[CH3:9])=[CH:12][N:13]=2)=[CH:39][C:38]([S:40]([NH2:43])(=[O:41])=[O:42])=[C:37]([F:44])[CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 667407195-(Bromomethyl)-4-chloro-2-fluorobenzenesulfonamideHCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

Product 1

HCID 667400214-Chloro-5-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzenesulfonamideYield 81.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (0.94 g, 2.49 mmol) and K2CO3 in acetone (5 mL) was added 5-(bromomethyl)-4-chloro-2-fluorobenzenesulfonamide (0.83 g, 2.73 mmol). After stirring 3 h, the reaction mixture was filtered. The filtrate was concentrated and purified by chromatography (silica, EtOAc-Hex) to afford the title compound (1.21 g). 1H-NMR (DMSO-d6, 400 MHz) δ 7.81 (d, J=7.8 Hz, 1H), 7.77 (s, 2H), 7.70 (d, J=9.7 Hz, 1H), 7.22-7.19 (m, 1H), 7.16 (s, 1H), 7.01-6.97 (m, 2H), 6.56-6.49 (m, 4H), 4.26 (s, 2H), 3.64 (s, 3H), 1.46 (s, 6H); MS (EI) m/z 598 [M]+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified by chromatography (silica, EtOAc-Hex)

Sources & evidence

ORD record
ord-8cade4a404bc4a80be879a94c4280e8e
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

Loading…