2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631305, compound

HRID 1431769Notes

Reaction equation

HRID 1431769 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].[NH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:30]=1)[C:24]([O:26][CH3:27])=[O:25].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+]>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:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:20][C:21]3[CH:22]=[C:23]([CH:28]=[C:29]([N:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)[CH:30]=3)[C:24]([O:26][CH3:27])=[O:25])=[C:3]([CH3:19])[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:5]2)=[CH:10][CH:9]=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 59631494HCID 59631494, compound

Product 1

HCID 59631305HCID 59631305, compound

Reagents, catalysts & solvents 2

HCID 54751079XPhos PalladacycleCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to Procedure Y using 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.300 g, 1.100 mmol), methyl 3-amino-5-morpholinobenzoate (0.260 g, 1.100 mmol), XPhos precatalyst (CAS 1028206-56-5; 0.074 g, 0.110 mmol), XPhos (0.052 g, 0.110 mmol), sodium tert-butoxide (0.26 g, 2.75 mmol), and toluene (2.2 mL). Purification by column chromatography (silica; 0-90% EtOAc in hexanes) afforded methyl 3-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-5-morpholinobenzoate as a yellow amorphous solid. Mass Spectrum (ESI) m/e=473.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bee71fa54c214431bdd0db6e79d23826
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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