Dimethylformamide → HCID 86651056, compound

HRID 2094417Notes

Reaction equation

HRID 2094417 reaction equation
[H-].[Na+].CN(C=O)C.[F:8][C:9]([F:13])([F:12])[CH2:10][OH:11].[F:14][C:15]1([F:36])[C:33]2[C:18](=[CH:19][C:20]3[O:24][C:23]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][C:26]=4F)=[N:22][C:21]=3[CH:32]=2)[C:17]([F:35])([F:34])[O:16]1>O>[F:36][C:15]1([F:14])[C:33]2[C:18](=[CH:19][C:20]3[O:24][C:23]([C:25]4[CH:26]=[CH:27][N:28]=[CH:29][C:30]=4[O:11][CH2:10][C:9]([F:13])([F:12])[F:8])=[N:22][C:21]=3[CH:32]=2)[C:17]([F:34])([F:35])[O:16]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 58148278HCID 58148278, compound

Product 1

HCID 86651056HCID 86651056, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 44 mg of 60% sodium hydride (in oil) and 2 ml of DMF was stirred at room temperature. To the mixture, a mixture solution of 0.11 g of 2,2,2-trifluoroethanol and 0.5 ml of DMF was added. The mixture solution was stirred for 15 minutes, and then, 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 was added and stirred at room temperature for one hour. 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 0.25 g of 5,5,7,7-tetrafluoro-2-[3-(2,2,2-trifluoroethoxy)pyridin-4-yl]-5,7-dihydro-furo[3′,4′:4,5]benzo[1,2-d]oxazole (hereinafter, referred to as “active compound 89”).

Workup

  1. stirringThe mixture solution was stirred for 15 minutes
  2. stirringstirred at room temperature for one hour
  3. extractionfollowed by extraction with ethyl acetate twice
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02d03f4a4e0f4262b6458f5306e40f35
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

Loading…