Water → HCID 22028180, compound

HRID 731565Notes

Reaction equation

HRID 731565 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:4][CH:3]=1.C([O-])(O)=[O:19].[Na+].OOS([O-])=O.[K+].[OH2:29]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)(=[O:19])=[O:29])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 22028196HCID 22028196, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22028180HCID 22028180, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-[(4-fluorophenyl)thio]-1H-pyrrolo[2,3-b]pyridine (3.36 g, 13.8 mmol) in acetone is treated with a solution of NaHCO3 (2.90 g, 34.5 mmol) in water. The reaction is then treated with Oxone®1 (25.5 g, 41.4 mmol), stirred for 3 h at 20° C., diluted with water, cooled in an ice-water bath and filtered. The filtercake is washed with water and vacuum dried to afford the title compound as a white solid 1.73 g, mp 212-213° C., characterized by mass spectral and NMR analyses. 12KHSO5.KHSO4.K2SO4, manufactured by DuPont, Wilmington, Del.

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationfiltered
  3. washThe filtercake is washed with water and vacuum
  4. customdried

Sources & evidence

ORD record
ord-f72647e1cb0b4ed48878c0afbedc332a
Source dataset
uspto-grants-2009_09
Patent number
US07585873B2

Reaction notes

Loading…