Water → HCID 44219398, compound

HRID 512111Notes

Reaction equation

HRID 512111 reaction equation
Br[C:2]1[N:3]=[C:4]([S:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1(C)C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][S:11]([C:4]2[C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=[C:2]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:3]=2)(=[O:13])=[O:12])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 44219554HCID 44219554, compound

Product 1

HCID 44219398HCID 44219398, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

200 mg (0.51 mM) of 5-bromo-3-[(4-chlorobenzyl)sulfonyl]-1-ethylpyrazin-2(1H)-one and 20 mg of tetrakis Pd(PPh3) in 4 ml of toluene were stirred for 10 min at room temperature under nitrogen atmosphere. 93.4 mg (0.77 mM) of phenyl boronic acid and 1.5 ml of a 2M cesium carbonate aqueous solution were added and the reaction mixture was refluxed under stirring for 1 h30. 10 ml of water and 10 ml of toluene were added, the organic layer was separated. The aqueous layer was extracted with toluene and the combined organic layer was separated and washed with water, dried on anhydrous sodium sulfate and concentrated under vacuum. The residue was further purified by silica gel column chromatography, using dichloromethane/dimethylketone (95/5) as eluant, to give 52 mg of 3-[(4-chlorobenzyl)sulfonyl]-1-ethyl-5-phenylpyrazin-2(1H)-one as a solid. Yield: 26%.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with toluene
  4. customthe combined organic layer was separated
  5. washwashed with water
  6. dry with materialdried on anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-976029b7770f43f2b62f623dee630bb8
Source dataset
uspto-grants-2015_08
Patent number
US09102632B2

Reaction notes

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