Ethyl trifluoroacetate → N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide

HRID 2199253Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:16])([F:15])[C:10]([O:12]CC)=O.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.O.CO>[Cl:17][C:18]1[N:19]=[CH:20][C:21]([CH2:24][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[N:1][C:10](=[O:12])[C:9]([F:8])([F:15])[F:16])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

In a mixture solvent of 25 mL of N,N-dimethylformamide and 10 ml of toluene, 4.7 g (0.05 mol) of 2-aminopyridine was dissolved. To the solution, 35.5 g (0.25 mol) of ethyl trifluoroacetate, 9.72 g (0.06 mol) of 2-chloro-5-chloromethylpyridine, and 8.28 g (0.06 mol) of potassium carbonate powder were added, followed by stirring at 65° C. for 18 hours. To the reaction liquid, 10 mL of methanol was added, and then the reaction liquid was added to 150 mL of hot water of 50° C. After being cooled to room temperature, the mixture was stirred for 1 hour. Crystals were filtered, and washed with 50 mL of water and 50 mL of toluene. The obtained crystals were dried under reduced pressure at 45° C. Thus, 13.78 g of the target compound was obtained (Percentage Yield: 87.5%).

Workup

additionwas added
customthe reaction liquid
temperatureAfter being cooled to room temperature
stirringthe mixture was stirred for 1 hour
filtrationCrystals were filtered
washwashed with 50 mL of water and 50 mL of toluene
customThe obtained crystals were dried under reduced pressure at 45° C

Sources & evidence

ORD record: ord-1b258716050346ecb5aa068af80f0c5b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09357776B2

Reaction notes

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