Acetone → HCID 9933190, compound

HRID 2300194Notes

Reaction equation

HRID 2300194 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:10]=2[C:11]2[CH:16]=[CH:15][C:14](SC)=[CH:13][CH:12]=2)[CH:7]=1.O[O:27][S:28]([O-:30])=O.[K+].[CH3:32]C(C)=O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([S:28]([CH3:32])(=[O:30])=[O:27])=[CH:15][CH:16]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 18376038HCID 18376038, compoundHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 9933190HCID 9933190, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 6-bromo-2-(4-fluorophenyl)-3-[4-(methylsulfanyl)phenyl]pyrazolo[1,5-a]pyridine (0.26 g 0.63 mmol) in acetone (30 ml) was added a solution of oxone (1.16 g 1.9 mmol) in water (10 ml). The reaction was stirred at room temperature for 20 hours, further oxone (1 g 1.7 mmol) in water (10 ml) was added and stirring was continued for 6 hours. The reaction mixture was poured into water (200 ml) and extracted with ethyl acetate (3×30 ml). The combined extracts were washed with water (30 ml), brine (30 ml) and dried. Removal of solvent gave a solid which was purified by biotage chromatography. Elution with cyclohexane ethyl acetate gave the title compound as a white solid (0.13 g 58%). MH+: 445, 447. NMR: (CDCl3) δ 3.13 (3H, s) 7.07 (2H, t) 7.29 (1H, dd) 7.45-7.55 (5H, m) 7.96 (2H, d) 8.67 (1H, s).

Workup

  1. stirringstirring
  2. waitwas continued for 6 hours
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washThe combined extracts were washed with water (30 ml), brine (30 ml)
  5. customdried
  6. customRemoval of solvent
  7. customgave a solid which
  8. customwas purified by biotage chromatography
  9. washElution with cyclohexane ethyl acetate

Sources & evidence

ORD record
ord-0382f8429d354b55b5e2370086dcd299
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

Loading…