Sodium Sulfite → 8-[1-(Chloromethyl)ethenyl]-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

HRID 15135Notes

Reaction equation

HRID 15135 reaction equation
[F:1][C:2]1[C:3]([O:16][CH3:17])=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([F:12])[C:6]=2[C:13]([CH3:15])=[CH2:14].O.O.O.O.O.O.O.[Cl-:25].[Ce+3].[Cl-].[Cl-].Cl[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C>[Cl:25][CH2:14][C:13]([C:6]1[C:7]([F:12])=[CH:8][N:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:16][CH3:17])[C:2]([F:1])=[CH:11]2)=[CH2:15]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 21585214Cerium trichloride heptahydrateHCID 23665760Sodium HypochloriteHCID 675270293,7-Difluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine

Product 1

HCID 675271518-[1-(Chloromethyl)ethenyl]-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 3,7-difluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine (820 mg, 3.5 mmol) in tert-butanol (50 ml) under argon was treated with cerium(III) chloride heptahydrate (1.29 g, 3.5 mmol) followed by a solution of sodium hypochlorite (12% w/v, 2.6 ml, 4.2 mmol). After 30 minutes stirring, saturated aqueous sodium sulphite solution (20 ml) was added. After 15 minutes stirring the mixture was extracted with ether (3×200 ml). The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica eluting a gradient of 0-50% ethyl acetate in hexane affording a white solid (320 mg, 34%).

Workup

  1. stirringAfter 15 minutes stirring the mixture
  2. extractionwas extracted with ether (3×200 ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica eluting a gradient of 0-50% ethyl acetate in hexane affording a white solid (320 mg, 34%)

Sources & evidence

ORD record
ord-1f05eff2dd94404e9c600e754f9a6940
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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