Sodium Bicarbonate → HCID 69217838, compound

HRID 2251077Notes

Reaction equation

HRID 2251077 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:13]2[N:14]=[C:15](SC)[N:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:21].O[O:30][S:31]([O-:33])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[C:43]([O-])(O)=O.[Na+]>C1COCC1.O.CO>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:13]2[N:14]=[C:15]([S:31]([CH3:43])(=[O:33])=[O:30])[N:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:20]([C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)=[O:21]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 59643065HCID 59643065, compound

Product 1

HCID 69217838HCID 69217838, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [7-(2,6-difluoro-phenyl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-(4-fluoro-phenyl)-methanone, 3, (4.6 g, 11.5 mmol) in THF:methanol (108 mL of 1:1 mixture) is added dropwise a solution of Oxone® (potassium peroxymonosulfate) (28.4 g, 46.1 mmol) in H2O (83 mL). After stirring the reaction for 1 hour at room temperature, the solution is poured into aqueous saturated NaHCO3. The aqueous phase is extracted three times with EtOAc and the combined organic phases are dried (MgSO4), filtered and concentrated in vacuo to afford 4.5 g of the desired product which is used without further purification.

Workup

  1. customthe reaction for 1 hour at room temperature
  2. extractionThe aqueous phase is extracted three times with EtOAc
  3. dry with materialthe combined organic phases are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afe7c2ebba0a4001a35201e4c15106c3
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

Loading…