Potassium Carbonate → HCID 66740663, compound

HRID 1627249Notes

Reaction equation

HRID 1627249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH3:25])[CH:18]=3)[C:15]([SH:26])=[N:14][CH:13]=2)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:27][C:28]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:27][C:28]1[CH:37]=[CH:36][C:35]([CH2:38][S:26][C:15]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([O:24][CH3:25])[CH:18]=3)[C:12]([C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)([CH3:11])[CH3:10])=[CH:13][N:14]=2)=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60027362Methyl 2-bromo-5-(bromomethyl)benzoateHCID 178492989HCID 178492989, compound

Product 1

HCID 66740663HCID 66740663, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluoro-3-methoxyphenyl)-1H-imidazole-2-thiol (700 mg, 1.7 mmol, 1.0 eq), methyl 2-bromo-5-(bromomethyl)benzoate (630 mg, 2.0 mmol, 1.2 eq) and potassium carbonate (350 mg, 2.6 mmol, 1.5 eq) in acetone (9 mL) was stirred at room temperature 1 h. The solids were filtered and the organics were concentrated and purified (silica, 0 to 60% EtOAc/Hex) to afford the title compound (900 mg, 83%). MS (EI) m/z 638.9 (MH+).

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe organics were concentrated
  3. custompurified (silica, 0 to 60% EtOAc/Hex)

Sources & evidence

ORD record
ord-7333e6b1bf774c2495201f36d088f9cc
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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