2-Amino-4-(trifluoromethyl)pyridine → HCID 118194803, compound

HRID 918790Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])=O.[NH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=1>C(O)C>[CH2:14]([S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:16]=[C:17]2[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=[CH:19][N:18]2[CH:2]=1)(=[O:13])=[O:12])[CH3:15]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1.0 g of 2-bromo-2′-ethylsulfonylacetophenone, 334 mg of 2-amino-4-trifluoromethylpyridine and 4 ml of ethanol was refluxed for 1 hour and concentrated under reduced pressure. A mixture of the residue, 250 mg of sodium bicarbonate and 1.5 ml of DMF was stirred at 130° C. for 1 hour. Water was poured to the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 190 mg of 2-(2-ethylsulfonylphenyl)-7-trifluoromethyl-imidazo[1,2-a]pyridine (hereinafter, referred to as Compound of Present Invention 8).

Workup

temperaturewas refluxed for 1 hour
concentrationconcentrated under reduced pressure
additionA mixture of the residue, 250 mg of sodium bicarbonate and 1.5 ml of DMF
additionWater was poured to the cooled reaction mixture
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-25c05e8c18f04a95a89c7395fd3483c1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271500B2

Reaction notes

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