Potassium Carbonate → HCID 66740290, compound

HRID 1627308Notes

Reaction equation

HRID 1627308 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][CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1>CC(C)=O>[C:43]([O:42][C:40]([N:37]1[CH2:38][CH2:39][CH: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)[CH2:35][CH2:36]1)=[O:41])([CH3:46])([CH3:44])[CH3:45]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

Product 1

HCID 66740290HCID 66740290, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (0.557 g, 1.48 mmol) and K2CO3 (0.306 g, 2.22 mmol) in acetone (4 mL) was added tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (0.431 g, 1.55 mmol). The reaction was heated at reflux. After 4 h, the reaction was concentrated and purified by column chromatography using Hex:EtOAc as eluents to afford the title compound (0.765 g) as a white solid. MS (EI) m/z 574 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux
  3. concentrationthe reaction was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-be1451ebb7534130ba5159353033e74e
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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