Potassium Carbonate → 7-Fluoro-2-(methoxy)-8-(2-oxiranyl)-1,5-naphthyridine

HRID 639024Notes

Reaction equation

HRID 639024 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[N:23]=3)[N:18]=[CH:17][C:16]=2[F:27])[OH:14])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:27][C:16]1[C:15]([CH:13]2[CH2:12][O:14]2)=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([O:25][CH3:26])=[N:23]2)=[N:18][CH:17]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 866033622-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

Product 1

HCID 590032567-Fluoro-2-(methoxy)-8-(2-oxiranyl)-1,5-naphthyridineYield 94.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-[3-fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl 4-methylbenzenesulfonate (10.5 g, 26.7 mmol) in anhydrous methanol (160 mL), cooled in an ice-bath, potassium carbonate (7.03 g, 50.9 mmol) was added. After 15 minutes with cooling, the mixture was stirred at room temperature for a further 1.75 hours. It was then diluted with water, extracted several times with dichloromethane, dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with dichloromethane, chloroform then 20% ethyl acetate in chloroform to afford the title product as an oil (5.55 g, 94%). MS (+ve ion electrospray) m/z 221 (M+H)+.

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureAfter 15 minutes with cooling
  3. extractionextracted several times with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on silica gel eluting with dichloromethane, chloroform

Sources & evidence

ORD record
ord-e07868c4754d46bb9fda651b07248082
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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