2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631286, compound

HRID 1431767Notes

Reaction equation

HRID 1431767 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:13]=2)[NH2:10])=[N:4][N:3]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=2)[N:24]=[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[C:22]=1[CH3:38].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:31][C:27]1[CH:26]=[C:25]2[C:30]([C:21]([NH:10][C:9]3[CH:11]=[C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[CH:13]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)[CH:8]=3)=[C:22]([CH3:38])[C:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[N:24]2)=[CH:29][CH:28]=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 59631507HCID 59631507, compound

Product 1

HCID 59631286HCID 59631286, compound

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to Procedure N using 3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-morpholinoaniline (0.034 g, 0.131 mmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.036 g, 0.131 mmol), sodium tert-butoxide (0.031 g, 0.327 mmol), XPhos precatalyst (CAS 1028206-56-5; 8.79 mg, 0.013 mmol), XPhos (6.23 mg, 0.013 mmol), and toluene (0.7 mL) to afford 7-fluoro-3-methyl-N-(3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(4-morpholinyl)phenyl)-2-(2-pyridinyl)-4-quinolinamine as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.79 (1H, s), 8.68-8.71 (1H, m), 8.07-8.15 (1H, m), 8.00 (1H, dd, J=7.6, 2.0 Hz), 7.88-7.91 (1H, m), 7.77 (1H, dd, J=10.3, 2.6 Hz), 7.48-7.54 (2H, m), 6.96 (1H, t, J=1.9 Hz), 6.72 (1H, t, J=1.7 Hz), 6.51 (1H, t, J=2.2 Hz), 3.70-3.74 (4H, m), 3.07-3.14 (4H, m), 2.52 (3H, s), 2.23 (3H, s). Mass Spectrum (ESI) m/e=497.1 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8d5ea495c6e04d8b9237331858fb1ba1
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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