Ethyl Acetate → HCID 89778755, compound

HRID 623298Notes

Reaction equation

HRID 623298 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[F:10][CH:11]([F:21])[C:12]([N:14]=[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][NH:16]1)=[O:13].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[F:21][CH:11]([F:10])[C:12]([N:14]=[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]1[CH2:2][C:3]1[CH:8]=[N:7][C:6]([F:9])=[CH:5][CH:4]=1)=[O:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 220506385-(Bromomethyl)-2-fluoropyridineHCID 178522122HCID 178522122, compound

Product 1

HCID 89778755HCID 89778755, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

128 mg (0.75 mmol) of 5-bromomethyl-2-fluoropyridine was dissolved in 3 ml of anhydrous DMF, 116 mg (0.68 mmol) of 2,2-difluoro-N-[pyridin-2(1H)-ylidene]acetamide was dissolved in 3 ml of anhydrous DMF and added thereto, and subsequently, 103 mg (0.75 mmol) of potassium carbonate was added thereto and the resulting mixture was stirred at 65° C. for 2 hours. After the reaction was completed, the reaction solution was returned to room temperature, and ethyl acetate and water were added thereto to perform liquid separation. The organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A small amount of hexane and diethyl ether were added thereto to precipitate crystals, and thus the crystals were collected and dried to obtain the subject material. Amount obtained 50 mg (yield 26%).

Workup

  1. additionadded
  2. customwas returned to room temperature
  3. customliquid separation
  4. washThe organic layer was washed with 1% hydrochloric acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionA small amount of hexane and diethyl ether were added
  8. customto precipitate crystals
  9. customthus the crystals were collected
  10. customdried
  11. customto obtain the subject material
  12. customAmount obtained 50 mg (yield 26%)

Sources & evidence

ORD record
ord-a5d6601bd9224299b57d2516d0c2f870
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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