Pyridine → Phenyl 2-(pyridin-3-yloxy)-5-(trifluoromethyl)phenylcarbamate

HRID 217876Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:9]=2[NH2:10])[CH:2]=1.N1C=CC=CC=1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][C:9]=2[NH:10][C:26](=[O:27])[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A yellow solution of 2-(pyridin-3-yloxy)-5-(trifluoromethyl)aniline (263 mg, 1.035 mmol) and pyridine (108 μL, 1.341 mmol) in dry THF (8 mL) was treated dropwise with phenyl chloroformate (156 μL, 1.242 mmol) during 5 min at 0° C. The resulting suspension yellow suspension was stirred at 0° C. for an additional 5 min and then allowed to warm up to room temperature and stirred for 3 h. The yellow suspension was filtered over cotton, washed with Et2O and diluted with EtOAc. The yellow solution was washed with sat. aqueous NaHCO3 (30 mL) and H2O (30 mL), dried and concentrated to dryness to give a yellow oil. Purification by column gave a tan solid. Yield: 300 mg (77%).

Workup

temperatureto warm up to room temperature
stirringstirred for 3 h
filtrationThe yellow suspension was filtered over cotton
washwashed with Et2O
additiondiluted with EtOAc
washThe yellow solution was washed with sat. aqueous NaHCO3 (30 mL) and H2O (30 mL)
customdried
concentrationconcentrated to dryness
customto give a yellow oil
customPurification by column
customgave a tan solid

Sources & evidence

ORD record: ord-d1c7a08ed469478ba74e61b4ef4b22f7
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198279B2

Reaction notes

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