Sodium Carbonate → [4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

HRID 2104508Notes

Reaction equation

HRID 2104508 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[C:17]2[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].[NH2:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:30][C:31]1[CH:36]=[C:35]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 16090325[4-Chloro-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone

Product 1

HCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of tetrakis(triphenylphosphine)palladium (0) (0.12, 0.1 mmol), 2N sodium carbonate (5 mL, 10 mmol), [4-chloro-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (from Example 1, 0.67 g, 2.0 mmol) in 20 mL of toluene and 5 mL of ethanol was added 3-aminobenzeneboronic acid (0.62 g, 4.0 mmol). The reaction mixture was heated to 80° C. for 1 hour, diluted with ethyl acetate, washed with water and dried over MgSO4. Removal of solvent under reduced pressure gave a crude product that was purified by silica gel chromatography eluting with ethyl acetate/hexanes (5% to 50%) to give the title compound as a pale yellow solid; MS (EI) m/z 393.3 (M+H)+; 1H NMR (DMSO-d6): δ 5.21 (s, 2H), 6.39 (d, J=8.8 Hz, 1H), 6.47 (s, 1H), 6.48 (d, J=9.4 Hz, 1H), 6.95 (t, J=9.4 Hz, 1H), 7.39 (t, J=7.5 Hz, 2H), 7.56 (t, J=8.7 Hz, 1H), 7.63 (d, J=8.2 Hz, 2H), 7.80 (t, J=7.8 Hz, 1H), 8.10 (d, J=8.6 Hz, 1H), 8.31 (d, J=6.7 Hz, 1H), 9.08 (s, 1H).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customRemoval of solvent under reduced pressure
  4. customgave a crude product that
  5. customwas purified by silica gel chromatography
  6. washeluting with ethyl acetate/hexanes (5% to 50%)

Sources & evidence

ORD record
ord-7d7a1157b80c42629dbc4cba4f941715
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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