2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 59631233, compound

HRID 1431529Notes

Reaction equation

HRID 1431529 reaction equation
[CH:1]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCC[CH2:2]1.[Cl:35][C:36]1[C:45]2[C:40](=[CH:41][C:42]([F:47])=[CH:43][C:44]=2[F:46])[N:39]=[C:38]([C:48]2[CH:53]=[C:52](Cl)[CH:51]=[CH:50][N:49]=2)[C:37]=1[CH3:55].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:35][C:36]1[C:45]2[C:40](=[CH:41][C:42]([F:47])=[CH:43][C:44]=2[F:46])[N:39]=[C:38]([C:48]2[CH:53]=[C:52]([CH:1]=[CH2:2])[CH:51]=[CH:50][N:49]=2)[C:37]=1[CH3:55]

Participants

6

Reactant 3

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 59631059HCID 59631059, compound

Product 1

HCID 59631233HCID 59631233, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.049 mmol), 4-chloro-2-(4-chloropyridin-2-yl)-5,7-difluoro-3-methylquinoline (0.10 g, 0.31 mmol), vinyl boronic acid MIDA ester (0.056 g, 0.31 mmol) and Pd2dba3 (0.011 g, 0.012 mmol) in toluene (3.1 mL) was added sodium tert-butoxide (0.074 g, 0.77 mmol). The reaction mixture was heated to 100° C. and stirring continued for 76 h. The crude product was purified by column chromatography on silica gel (0 to 50% hexanes/EtOAc) to give the desired product 4-chloro-5,7-difluoro-3-methyl-2-(4-vinylpyridin-2-yl)quinoline. Mass Spectrum (ESI) m/e=317.0 (M+1).

Workup

  1. customThe crude product was purified by column chromatography on silica gel (0 to 50% hexanes/EtOAc)

Sources & evidence

ORD record
ord-97cef04d538d4c8e84ab312b2f1c975e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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