Pyridine → HCID 68614849, compound

HRID 928676Notes

Reaction equation

HRID 928676 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11]([NH2:13])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11]#[N:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 90384503HCID 90384503, compound

Product 1

HCID 68614849HCID 68614849, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (143 mg, 0.572 mmol) of Step 1 was dissolved in THF. Pyridine (0.138 mL, 1.71 mmol) was added thereto, trifluoroacetic anhydride (0.119 mL, 0.858 mmol) was added thereto at −5° C. to 0° C., and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. After diluted with ethyl acetate, the resultant was washed with 1 N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure to thus obtain the title compound without purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionAfter diluted with ethyl acetate
  3. washthe resultant was washed with 1 N hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine, and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-48f57efa9b94406989321198566f086d
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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