Methanol → HCID 58148144, compound

HRID 2094416Notes

Reaction equation

HRID 2094416 reaction equation
[F:1][C:2]1([F:23])[C:20]2[C:5](=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][N:15]=[CH:14][C:13]=4F)=[N:9][C:8]=3[CH:19]=2)[C:4]([F:22])([F:21])[O:3]1.[C:24](=O)([O-])[O-:25].[K+].[K+].CO>O>[F:23][C:2]1([F:1])[C:20]2[C:5](=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][N:15]=[CH:14][C:13]=4[O:25][CH3:24])=[N:9][C:8]=3[CH:19]=2)[C:4]([F:21])([F:22])[O:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 58148278HCID 58148278, compound

Product 1

HCID 58148144HCID 58148144, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.28 g of 5,5,7,7-tetrafluoro-2-(3-fluoropyridin-4-yl)-5,7-dihydro-furo[3′,4′:4,5]benzo[1,2-d]oxazole, 0.24 g of potassium carbonate and 3 ml of methanol was stirred while heating at 60° C. for 3.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.13 g of 5,5,7,7-tetrafluoro-2-(3-methoxypyridin-4-yl)-5,7-dihydro-furo[3′,4′:4,5]benzo[1,2-d]oxazole (hereinafter, referred to as “active compound 88”).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe combined organic layers were washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76881e22d2fa4d939db1e608390106ec
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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