Dimethylformamide → HCID 66880170, compound

HRID 2094432Notes

Reaction equation

HRID 2094432 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[OH:18])[O:9][C:6]2=[N:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:32](I)([CH3:34])[CH3:33]>O>[CH:32]([O:18][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:12]=1[C:10]1[O:9][C:6]2[C:5]([N:11]=1)=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][N:7]=2)([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodide2×HCID 11430Potassium Carbonate2×HCID 136331269HCID 136331269, compound

Product 1

HCID 66880170HCID 66880170, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.26 g of 4-(6-trifluoromethyl-oxazolo[5,4-b]pyridin-2-yl)pyridin-3-ol, 0.14 g of potassium carbonate and 3 ml of DMF, 0.17 g of isopropyl iodide was added at room temperature and stirred while heating at 60° C. for 1.5 hours. To the reaction solution, 38 mg of potassium carbonate and 47 mg of isopropyl iodide were added, and the reaction solution was stirred while heating at 60° C. for two hours. The reaction solution was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and 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 0.16 g of 2-(3-isopropoxypyridin-4-yl)-6-trifluoromethyl-oxazolo[5,4-b]pyridine (hereinafter, referred to as “active compound 160”).

Workup

  1. additionwas added at room temperature
  2. stirringthe reaction solution was stirred
  3. temperaturewhile heating at 60° C. for two hours
  4. temperatureThe reaction solution was cooled to room temperature
  5. extractionfollowed by extraction with ethyl acetate twice
  6. washThe combined organic layers were washed with water
  7. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10bfe7cfce854bc88e6f0c858f308f17
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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