4-(Trifluoromethyl)aniline → 2,5-bis(4-nitrophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrrole

HRID 2364815Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>C(O)(=O)C.O.C(OCC)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:31]([C:30]3[CH:32]=[CH:33][C:27]([C:26]([F:25])([F:34])[F:35])=[CH:28][CH:29]=3)[C:13]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 170 °C

Procedure

To a slurry of the product from Example 1A (1.00 g, 3.05 mmol) in acetic acid (30 mL) was added 4-(trifluoromethyl)aniline (1.9 mL, 15 mmol). The mixture was heated to 170° C. for 15 minutes under microwave irradiation. The cooled mixture was diluted with water and diethyl ether and stirred vigorously for 15 minutes and then filtered. The crude product was purified by chromatography on silica gel eluting with a solvent gradient of 0-30% ethyl acetate in hexane. Product containing fractions were combined and concentrated under reduced pressure and then triturated with diethyl ether to give the title compound (110 mg, 8% yield).

Workup

filtrationfiltered
customThe crude product was purified by chromatography on silica gel eluting with a solvent gradient of 0-30% ethyl acetate in hexane
additionProduct containing fractions
concentrationconcentrated under reduced pressure
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-87a36938834e43549321aa6f3f868a4f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691938B2

Reaction notes

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