Sodium Carbonate → HCID 10761534, compound

HRID 275762Notes

Reaction equation

HRID 275762 reaction equation
FC(F)(F)S([C:6]1[C:7](=[O:27])[N:8]([CH3:26])[C:9]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:11]=1)(=O)=O.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:11]=[C:6]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:7](=[O:27])[N:8]([CH3:26])[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 18315870HCID 18315870, compound

Product 1

HCID 10761534HCID 10761534, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-trifluoromethanesulfonyl-5-(4-methoxyphenyl)-6-(4-pyridyl)-1-methyl-1H-pyridin-2-one (0.055 g), benzeneboronic acid (0.25 g) and aqueous sodium carbonate (2M; 2 cm3) in dimethoxyethane (5 cm3) was degassed and purged with nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium (0) (0.1 g) was added and the mixture was refluxed under nitrogen for 2 hours. The mixture was diluted with water (10 cm3) and extracted with ethyl acetate (3×10 cm3). The extracts were dried (sodium sulphate), filtered and concentrated. Preparative thin layer chromatography, eluting with 95:5 dichloromethane-methanol, gave 5-(4-methoxyphenyl)-6-(4-pyridyl)-3-phenyl-1-methyl-1H-pyridin-2-one (0.028 g; 61%) as a pale pink foam. Recrystallised to give a beige powder m.p. 183-185° C. (EtOAc-hexane). δH (360 MHz; CDCl3) 3.39 (3 H, s, NCH3), 3.73 (3 H, s, OCH3), 6.69 (2 H, d, J 9, methoxyphenyl H-2), 6.90 (2 H, d, J 9, methoxyphenyl H-3), 7.13 (2 H, d, J 6, pyridyl H-3), 7.35-7.44 (3 H, m, 3 of Ph), 7.59 (1 H, s, pyridone H-4), 7.77 (2 H, d, J 8, 2 of Ph) and 8.60 (2 H, d, J 6, pyridyl H-2); m/z (ESP+) 369 (MH+; 100%).

Workup

  1. customwas degassed
  2. custompurged with nitrogen at room temperature
  3. additionTetrakis(triphenylphosphine)palladium (0) (0.1 g) was added
  4. temperaturethe mixture was refluxed under nitrogen for 2 hours
  5. additionThe mixture was diluted with water (10 cm3)
  6. extractionextracted with ethyl acetate (3×10 cm3)
  7. dry with materialThe extracts were dried (sodium sulphate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washPreparative thin layer chromatography, eluting with 95:5 dichloromethane-methanol

Sources & evidence

ORD record
ord-291e20acf00c4257bf4dc9fd2add9078
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Reaction notes

Loading…