Ethanol → [4-(3,5-Difluorophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

HRID 2104590Notes

Reaction equation

HRID 2104590 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([F:31])[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O.C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[C:11]3[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH:28]=[C:29]([F:31])[CH:30]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 16090325[4-Chloro-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone

Product 1

HCID 66913505[4-(3,5-Difluorophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)MethanoneYield 48%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To (4-chloro-8-trifluoromethyl-quinoline-3-yl)-phenyl-methanone (150 mg, 0.448 mmol), 3,5-difluorophenyl boronic acid (141 mg, 0.895 mmol), tetrakis(triphenylphosphine) palladium (52 mg, 0.045 mmol), sodium carbonate (50 mg, 1.41 mmol) in water (750 ml), glyme (2 ml), and ethanol (350 ml), was subjected to micro wave conditions (140° C., 300 watts, 300 sec.). The resulting dark red-brown mixture was filtered concentration in vacuo. Reverse phase gradient HPLC (CH3CN, H2O) afforded the title compound as a yellow powder (88 mg, 48%). MS (ESI) m/z 414; HRMS: calcd for C23H12F5NO, 413.0839; found (ESI, [M+H]+), 414.0911.

Workup

  1. customwas subjected to micro wave conditions (140° C., 300 watts, 300 sec.)
  2. filtrationThe resulting dark red-brown mixture was filtered
  3. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-daddaa5a6c344b74a18caf6f4528ee76
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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