Cesium carbonate → HCID 68014787, compound

HRID 1747834Notes

Reaction equation

HRID 1747834 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:20][CH3:21])[C:5](=[O:19])[N:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[CH:10][CH:9]=2)[CH:7]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[C:41]1(B(O)O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:21][O:20][C:4]1[C:5](=[O:19])[N:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=[CH:10][CH:9]=2)[CH:7]=[C:2]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 89586553HCID 89586553, compound

Product 1

HCID 68014787HCID 68014787, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5-chloro-3-methoxy-1-(1-phenyl-1H-pyrazol-5-yl)pyrazin-2(1H)-one (245 mg), tri-tert-butylphosphine (25.0 mg), Pd2(dba)3 (37.0 mg), cesium carbonate (791 mg) and 1,4-dioxane (10.0 ml) was added phenylboronic acid (120 mg) at room temperature. The reaction mixture was heated using a microwave reactor at 95° C. for 1.5 hr. The reaction mixture was concentrated, dichloromethane was added, and the mixture was washed with saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (18.0 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. customat 95° C.
  3. customfor 1.5 hr
  4. concentrationThe reaction mixture was concentrated
  5. additiondichloromethane was added
  6. washthe mixture was washed with saturated brine
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-86158e96c11344c78fe1212f173049e3
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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