Dimethylformamide → HCID 66880045, compound

HRID 1913678Notes

Reaction equation

HRID 1913678 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.[CH2:32](I)[CH3:33]>O>[CH2:32]([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)[CH3:33]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6340Iodoethane2×HCID 11430Potassium Carbonate2×HCID 136331269HCID 136331269, compound

Product 1

HCID 66880045HCID 66880045, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.25 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, a mixture of 0.15 g of ethyl iodide and 1 ml of DMF was added at room temperature and stirred while heating at 60° C. for 1.5 hours. To the reaction mixture, 70 mg of potassium carbonate and 53 mg of iodoethane were added, and the reaction solution was stirred while heating at 60° C. for 3.5 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 60 mg of 2-(3-ethoxypyridin-4-yl)-6-trifluoromethyl-oxazolo[5,4-b]pyridine (hereinafter, referred to as “active compound 161”).

Workup

  1. additionwas added at room temperature
  2. stirringthe reaction solution was stirred
  3. temperaturewhile heating at 60° C. for 3.5 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-cae0cb11b13247a7808fdc6e2c3b3352
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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