2,4,6-Trifluoroaniline → HCID 86643795, compound

HRID 1802456Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7](Cl)[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3.[F:18][C:19]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[C:20]=1[NH2:21].CC(C)([O-])C.[Na+]>C1COCC1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:21][C:20]3[C:19]([F:18])=[CH:25][C:24]([F:26])=[CH:23][C:22]=3[F:27])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 9-bromo-1,5-dichlorobenzo[c]-2,6-naphthyridine (800 mg, 2.4 mmol) in THF (10 mL) were added 2,4,6 trifluoroaniline (359 mg, 2.4 mmol) and sodium tert-butoxide (703 mg, 7.32 mmol) and the reaction mixture was heated to 85° C. for 45 min. The solution was cooled to room temperature, quenched with methanol and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100% hexane to 100% EtOAc, gradient elution) to afford 9-bromo-1-chloro-N-(2,4,6-trifluorophenyl)benzo[c]-2,6-naphthyridin-5-amine. 9-Bromo-1-chloro-N-(2,4,6-trifluorophenyl)benzo[c]-2,6-naphthyridin-5-amine was taken up in THF (10 mL) and 6 N HCl (10 mL) and heated to 85° C. for 2 hr. The reaction was cooled to room temperature, neutralized with saturated NaHCO3 and extracted with EtOAc. The organic layers were dried over Mg2SO4, filtered, and concentrated. Column chromatography on silica gel (100% hexane to 100% EtOAc) provided the title compound.

Workup

temperatureThe solution was cooled to room temperature
customquenched with methanol
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (100% hexane to 100% EtOAc, gradient elution)

Sources & evidence

ORD record: ord-0e62d99562bb4b3294fd5d6a790e01c6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349865B2

Reaction notes

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