Ethyl Acetate → N-(4'-trifluoromethoxybiphenyl-2-yl)-3-methyl-pyrazine-2-carboxamide

HRID 1919478Notes

Reaction equation

HRID 1919478 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[C:22]([CH3:23])=[N:21][CH:20]=[CH:19][N:18]=1)=[O:16].[F:24][C:25]([F:38])([F:37])[O:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1.C(OCC)(=O)C>O.C1(C)C=CC=CC=1>[F:24][C:25]([F:37])([F:38])[O:26][C:27]1[CH:32]=[CH:31][C:30]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([C:17]2[C:22]([CH3:23])=[N:21][CH:20]=[CH:19][N:18]=2)=[O:16])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 227270174-Trifluoromethoxyphenylboric acidHCID 66750835N-(2-bromophenyl)-3-methylpyrazine-2-carboxamide

Product 1

HCID 66750778N-(4'-trifluoromethoxybiphenyl-2-yl)-3-methyl-pyrazine-2-carboxamideYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of sodium carbonate (0.31 g: 1.5 mmole) in 5 mL of water was added to a solution of N-(2-bromophenyl)-3-methylpyrazine-2-carboxamide (0.4 g: 1.4 mmole) and 4-trifluoromethoxyphenyl boric acid (0.31 g: 1.5 mmole) in 10 mL of toluene, followed by addition of tetrakis(triphenyl-Phosphine)palladium (0) (0.1 g: 0.09 mmole). After heating under reflux condition for 6 hours under argon atmosphere, the reaction mixture was cooled to room temperature, and admixed with ethyl acetate and water, followed by separation. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the subject compound (0.35 g).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux condition for 6 hours under argon atmosphere
  3. customfollowed by separation
  4. washThe organic layer was washed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f3f62fee887442ab9bc886d2bcbc89e
Source dataset
uspto-grants-2012_05
Patent number
US08168638B2

Reaction notes

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