Potassium Carbonate → HCID 58629944, compound

HRID 1391736Notes

Reaction equation

HRID 1391736 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:4]=1.[SH:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:22]([CH3:33])[CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:33][C:22]1[CH:21]=[C:20]([S:19][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=3)[N:4]=2)[CH:32]=[CH:31][C:23]=1[O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 69207805HCID 69207805, compound

Product 1

HCID 58629944HCID 58629944, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the 2-(bromomethyl)-6-[4-(trifluoromethyl)phenyl]pyridine (238 mg, 0.75 mmol), ethyl (4-mercapto-2-methylphenoxy)acetate (84 mg, 0.37 mmol) and K2CO3 (57 mg, 0.41 mmol) in MeCN (5 mL) was stirred at rt, under nitrogen overnight. The mixture was then partitioned between water and EtOAc and the layers separated. The organic layer was then washed with water and brine, dried (MgSO4), filtered and reduced. Purification by SPE (silica, 2 g cartridge) eluting with CHCl3:cyclohexane (5:1) afforded the title compound (160 mg).

Workup

  1. customThe mixture was then partitioned between water and EtOAc
  2. customthe layers separated
  3. washThe organic layer was then washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customPurification by SPE (silica, 2 g cartridge)
  7. washeluting with CHCl3:cyclohexane (5:1)

Sources & evidence

ORD record
ord-675d90246a6f46db99efc20f12755876
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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