Isopropanol → HCID 66880565, compound

HRID 2094398Notes

Reaction equation

HRID 2094398 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.[CH3:21][CH:22]([OH:24])[CH3:23].[H-].[Na+]>O>[CH:22]([O:24][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1)([CH3:23])[CH3:21]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 66880565HCID 66880565, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole and 3 ml of 2-propanol, 52 mg of 60% sodium hydride (in oil) was added while ice-cooling. The mixture was stirred for 1.5 hours and then heated to room temperature and stirred for 1.5 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 0.12 g of 2-(3-isopropoxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 70”).

Workup

  1. additionwas added while ice-
  2. temperaturecooling
  3. stirringstirred for 1.5 hours
  4. extractionfollowed by extraction with ethyl acetate twice
  5. washThe combined organic layers were washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e59cf1c109fc4ff2b660d0b41d34d207
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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