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

HRID 2199254Notes

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: 62.5 °C

Procedure

In 30 mL of dimethylformamide and 20 mL of toluene, 9.4 g (0.1 mol) of 2-aminopyridine was dissolved. To this solution, 14.2 g (0.1 mol) of ethyl trifluoroacetate was added, followed by stirring at 60 to 65° C. for 7 hours. Subsequently, 16.2 g (0.1 mol) of 2-chloro-5-chloromethylpyridine and 16.6 g (0.12 mol) of potassium carbonate were added thereto, followed by stirring at 60 to 65° C. for 18 hours. To the reaction liquid, 15 mL of methanol was added. Then the reaction liquid was added to 150 mL of hot water of 50° C., and the mixture was cooled to room temperature. Crystals were filtered, and washed with 50 mL of water and 75 mL of toluene. The obtained crystals were dried under reduced pressure at 60° C. Thus, 20.6 g of the target compound was obtained (Percentage Yield: 65.4%).

Workup

stirringby stirring at 60 to 65° C. for 18 hours
additionwas added
customThen the reaction liquid
temperaturethe mixture was cooled to room temperature
filtrationCrystals were filtered
washwashed with 50 mL of water and 75 mL of toluene
customThe obtained crystals were dried under reduced pressure at 60° C

Sources & evidence

ORD record: ord-1255f88cc0144b75a168898f200eef88
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09357776B2

Reaction notes

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