(2-Methylpropyl)boronic acid → HCID 86684978, compound

HRID 1505741Notes

Reaction equation

HRID 1505741 reaction equation
Cl[C:2]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)=[N:7]2.[CH2:21](B(O)O)[CH:22]([CH3:24])[CH3:23].C1(P(C2CCCCC2)[C:35]2C=CC=[CH:37][C:36]=2[C:41]2C(OC)=CC=CC=2OC)CCCCC1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].O>[CH3:20][C:15]1[CH:14]=[C:13]([C:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][C:10]([CH2:35][CH:36]([CH3:41])[CH3:37])=[CH:11][C:2]=3[CH2:21][CH:22]([CH3:24])[CH3:23])[N:7]=2)[CH:18]=[C:17]([CH3:19])[CH:16]=1

Participants

8

Reactant 4

HCID 2734395(2-Methylpropyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 86684979HCID 86684979, compound

Product 1

HCID 86684978HCID 86684978, compoundYield 592.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5,7-dichloro-2-(3,5-dimethylphenyl)quinoline (4.8 g, 15.9 mmol), isobutylboronic acid (6.48 g, 63.5 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.04 g, 2.54 mmol), Pd2(dba)3 (0.582 g, 0.635 mmol), potassium phosphate monohydrate (36.6 g, 159 mmol) and 2 mL of water were mixed in 240 mL of toluene. The system was degassed with nitrogen for 20 minutes and refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with dichloromethane. The product was purified by column chromatography (4:1 to 1:1 hexanes/ethyl acetate, v/v) to give 5.2 g (41% yield) of 2-(3,5-dimethylphenyl)-5,7-diisobutylquinoline, which was confirmed by GCMS.

Workup

  1. customThe system was degassed with nitrogen for 20 minutes
  2. temperaturerefluxed overnight
  3. filtrationthe reaction mixture was filtered through a Celite® plug
  4. washeluted with dichloromethane
  5. customThe product was purified by column chromatography (4:1 to 1:1 hexanes/ethyl acetate, v/v)

Sources & evidence

ORD record
ord-f5e345a238764c0b9efaf0156033e325
Source dataset
uspto-grants-2015_12
Patent number
US09217004B2

Reaction notes

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