Potassium Carbonate → 4-(4-Fluoro-3-(trifluoromethyl)phenoxy)-8-nitroquinoline

HRID 1469774Notes

Reaction equation

HRID 1469774 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24].C([O-])([O-])=O.[K+].[K+]>CC#N>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[C:11]3[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:18][C:17]=1[C:23]([F:24])([F:25])[F:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6018544-Fluoro-3-(trifluoromethyl)phenolHCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 716778824-(4-Fluoro-3-(trifluoromethyl)phenoxy)-8-nitroquinolineYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared following the procedure described in Intermediate-11, step-3 using 4-chloro-8-nitroquinoline (Intermediate-11, step-2, 250 mg, 1.20 mmol), 4-fluoro-3-(trifluoromethyl)phenol (430 mg, 2.40 mmol), K2CO3 (479 mg, 3.60 mmol) in CH3CN (5 mL) to afford 380 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 10.75 (s, 1H), 8.82 (d, J=5.4 Hz, 1H), 7.92 (m, 1H), 7.86-7.81 (m, 3H), 7.31 (t, J=9.6 Hz, 1H), 6.90 (d, J=5.1 Hz, 1H); MS (m/z): 353.14 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-dffbd719fb97431c8fa7d6cb8d6df340
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…