Sodium Sulfite → HCID 66801400, compound

HRID 2366299Notes

Reaction equation

HRID 2366299 reaction equation
[Br:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[S:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[S:8][C:4]=2[CH:5]=[N+:6]([O-:27])[CH:7]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66801347HCID 66801347, compound

Product 1

HCID 66801400HCID 66801400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-2-(2-chloro-6-fluoro-phenyl)thiazolo[5,4-c]pyridine (2.0 mmol, 690 mg) in DCM (20 mL) was added mCPBA (5. 2 mmol, 890 mg). The mixture was stirred at room temperature for 5 hours. A solution of 1 M Na2SO3 (10 mL) was then added. The mixture was then stirred at room temperature for 1 hour. A solution of sat. NaHCO3 was added. The layers were separated. The aqueous layer was extracted with DCM. Then the combined organics were dried (Na2SO4), filtered and concentrated to give the title compound as an off-white solid which was used in the next step without purification. LCMS (ESI) m/z 360.9 [M+H+].

Workup

  1. stirringThe mixture was then stirred at room temperature for 1 hour
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialThen the combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e60d66973e934d578683c1b29ca4a5cc
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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