1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

HRID 2190811Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[OH:22].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[OH:22])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 0.69 g of 3-bromo isonicotinic acid, 0.60 g of 2-amino-4-(trifluoromethyl)phenol, 1.00 g of WSC and 6 ml of pyridine was stirred while heating at 80° C. for two hours. The reaction mixture was cooled to room temperature, and then concentrated. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixture solvent of ethyl acetate and hexane to give 0.29 g of 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
additionWater was added to the residue
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
washThe residue was washed with a mixture solvent of ethyl acetate and hexane

Sources & evidence

ORD record: ord-42f877abbec44d09bd6c8e997d889726
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324387B2

Reaction notes

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