2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631056, compound

HRID 1431763Notes

Reaction equation

HRID 1431763 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=2)[N:23]=[C:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[C:21]=1[CH3:37].CC(C)([O-])C.[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].C1(C)C=CC=CC=1>[F:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([NH:1][C:2]3[CH:3]=[C:4]([CH:10]=[C:11]([N:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)[CH:12]=3)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])=[C:21]([CH3:37])[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[N:23]2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 59631117HCID 59631117, compound

Product 1

HCID 59631056HCID 59631056, compound

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to Procedure Y using 3-amino-N,N-dimethyl-5-morpholinobenzamide (0.046 g, 0.183 mmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)-quinoline (0.050 g, 0.183 mmol), sodium tert-butoxide (0.035 g, 0.367 mmol), XPhos (8.7 mg, 0.018 mmol), XPhos precatalyst (CAS 1028206-56-5; 0.012 g, 0.018 mmol), and toluene (1.0 mL) to afford 3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-N,N-dimethyl-5-(4-morpholinyl)benzamide as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.66-8.71 (1H, m), 8.60 (1H, s), 8.09 (1H, dd, J=9.4, 6.3 Hz), 7.99 (1H, td, J=7.7, 1.8 Hz), 7.87 (1H, dt, J=7.8, 1.2 Hz), 7.71-7.77 (1H, m), 7.45-7.52 (2H, m), 6.41-6.46 (1H, m), 6.35-6.41 (1H, m), 5.95-5.98 (1H, m), 3.68-3.73 (4H, m), 3.04-3.11 (4H, m), 2.82-2.91 (6H, m), 2.21 (3H, s). Mass Spectrum (ESI) m/e=486.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-afcd3597e4a44fae8181fe7227619976
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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