Sodium Carbonate → N-Quinolin-7-yl-6-(4-trifluoromethylphenyl)-nicotinamide

HRID 494264

Reaction equation

HRID 494264 reaction equation
Cl[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCOC(C)=O.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>[N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:19]=[CH:20][C:2]([C:26]4[CH:27]=[CH:28][C:23]([C:22]([F:33])([F:32])[F:21])=[CH:24][CH:25]=4)=[N:3][CH:4]=3)[CH:18]=2)[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 445789876-Chloro-N-quinolin-7-yl-nicotinamide

Product 1

HCID 44578937N-Quinolin-7-yl-6-(4-trifluoromethylphenyl)-nicotinamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-N-quinolin-7-yl-nicotinamide (D70) (40 mg, 0.14 mmol) in DME (0.9 ml) under an argon atmosphere was added 4-trifluoromethylphenylboronic acid (33 mg, 0.17 mmol), 2M sodium carbonate solution (0.17 ml) and tetrakis(triphenylphosphine)palladium (0) (8 mg, 0.007 mmol). The reaction was heated at reflux until complete by tlc, then cooled to room temperature and diluted with EtOAc and dried over MgSO4. The solvent was removed in vacuo and the resultant crude product was purified by SPE column chromatography. Elution with 75% EtOAc in 40-60° C. petroleum ether gave the title compound as an off-white solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 9.31 (dd, 1H), 8.83 (dd, 1H), 8.46 (dd, 1H), 8.39 (dd, 1H), 8.20 (m, 3H), 8.07 (d, 1H), 7.94 (dd, 1H), 7.89 (d, 1H), 7.79 (d, 2H), 7.40 (dd, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux until complete by tlc
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe resultant crude product was purified by SPE column chromatography
  6. washElution with 75% EtOAc in 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-3804f545fe4b4c91a07d363bb8bdb01c
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Linked notes

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