Methanol → HCID 22139730, compound

HRID 1825871Notes

Reaction equation

HRID 1825871 reaction equation
[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](SC)=[N:10]2.O[O:25][S:26]([O-:28])=O.[K+].[CH3:30]O>O>[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:26]([CH3:30])(=[O:28])=[O:25])=[N:10]2

Participants

5

Reactant 3

HCID 887MethanolHCID 22139704HCID 22139704, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22139730HCID 22139730, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.25 g of 5-(2,4-difluoro-phenoxy)-6-methoxy-2-methylsulfanyl-quinoline in 10 mL of methanol was treated with aqueous OXONE™ solution (1.3 g in 5 mL H2O) and stirred for 2 hours at room temperature. The reaction mixture was partitioned between water and dichloromethane, the organic layer was dried (MgSO4), and the solvent was removed under vacuum. The solid residue was dissolved in a minimum amount of dichloromethane and washed through a silica gel plug to remove the baseline impurities. Elution with 30% EtOAc/hexane yielded 0.11 g (38%) of 5-(2,4-difluoro-phenoxy)-2-methanesulfonyl-6-methoxy-quinoline 701 ([M+H]+)=366, as white crystals.

Workup

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customthe solvent was removed under vacuum
  4. dissolutionThe solid residue was dissolved in a minimum amount of dichloromethane
  5. washwashed through a silica gel plug
  6. customto remove the baseline impurities
  7. washElution with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-8c33fe9a989d4b62aee5328d439cb55b
Source dataset
uspto-grants-2006_05
Patent number
US07049325B2

Reaction notes

Loading…