Potassium Carbonate → HCID 67508044, compound

HRID 1431752Notes

Reaction equation

HRID 1431752 reaction equation
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Cl[C:36]1[C:45]2[C:40](=[CH:41][C:42]([F:46])=[CH:43][CH:44]=2)[N:39]=[C:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=2)[C:37]=1[CH3:53].[NH2:54][C:55]1[CH:56]=[C:57]([CH:62]=[C:63]([N:65]2[CH2:70][CH2:69][O:68][CH2:67][CH2:66]2)[CH:64]=1)[C:58]([NH:60][CH3:61])=[O:59].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[F:46][C:42]1[CH:41]=[C:40]2[C:45]([C:36]([NH:54][C:55]3[CH:56]=[C:57]([CH:62]=[C:63]([N:65]4[CH2:66][CH2:67][O:68][CH2:69][CH2:70]4)[CH:64]=3)[C:58]([NH:60][CH3:61])=[O:59])=[C:37]([CH3:53])[C:38]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)=[N:39]2)=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 59631218HCID 59631218, compound

Product 1

HCID 67508044HCID 67508044, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

Prepared according to Procedure X using palladium (II) acetate (2.1 mg, 9.17 μmol), XPhos (0.013 g, 0.028 mmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.050 g, 0.183 mmol), 3-amino-N-methyl-5-morpholinobenzamide (0.043 g, 0.183 mmol), potassium carbonate (0.063 g, 0.458 mmol), and tert-butanol (1 mL). Purification using column chromatography (silica; 0-5% methanol in DCM) afforded 3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-N-methyl-5-(4-morpholinyl)benzamide as a yellow amorphous solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.70-8.76 (1H, m), 7.80-7.95 (3H, m), 7.72-7.79 (1H, m), 7.35-7.44 (1H, m), 7.14-7.23 (1H, m), 6.88-6.96 (1H, m), 6.53-6.59 (1H, m), 6.36-6.43 (1H, m), 6.21-6.32 (1H, m), 6.15 (1H, br. s.), 3.76-3.84 (4H, m), 3.07-3.14 (4H, m), 2.93 (3H, d, J=4.7 Hz), 2.33 (3H, s). Mass Spectrum (ESI) m/e=472.1 (M+1).

Workup

  1. customPrepared
  2. customPurification

Sources & evidence

ORD record
ord-d37c49ebfcae4feb9adbb793b3266303
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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