Potassium Carbonate → HCID 58531623, compound

HRID 1889713Notes

Reaction equation

HRID 1889713 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:13]([Cl:14])=[CH:12][CH:11]=[C:4]([C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])[CH:3]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22117812HCID 22117812, compound

Product 1

HCID 58531623HCID 58531623, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

3-Bromo-4-chloro-N-methoxy-N-methylbenzamide (1.0 mg, 3.8 mmol, 1.0 eq) and 4-chloro phenyl boronic acid (787 mg, 5 mmol, 1.3 eq) was dissolved in toluene and stirred for 10 minutes. The solution was purged with nitrogen for 10 minutes and degassed under vacuum. Tetrakis triphenylphosphinepalladium (223 mg, 0.19 mmol, 0.05 eq) and K2CO3 (696 mg, 5 mmol, 1.3 eq) were added to the reaction. The mixture was refluxed for 12 h under nitrogen and the volatiles were removed under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (60-120) eluting with 5-10% ethyl acetate/hexane to afford the desired compound (1 g, 90%). 1H NMR (400 MHz, CD3OD) δ 3.37-3.39 (s, 3H), 3.60-3.64 (s, 3H), 7.10-7.13 (t, 1H), 7.25-7.27 (t, 1H), 7.43-7.48 (m, 3H), 7.60-7.63 (m, 3H). MS (ESI): 310.2 (M+).

Workup

  1. customThe solution was purged with nitrogen for 10 minutes
  2. customdegassed under vacuum
  3. temperatureThe mixture was refluxed for 12 h under nitrogen
  4. customthe volatiles were removed under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried with anhydrous Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel (60-120)
  10. washeluting with 5-10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c159a7376154578bd9e07167e87c2a5
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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