(2-Methylpropyl)boronic acid → 2-(3,5-Dimethylphenyl)-6,7-diisobutylquinoline

HRID 1505744Notes

Reaction equation

HRID 1505744 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]=[C:7]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)[CH:6]=[CH:5]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:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([CH2:35][CH:36]([CH3:41])[CH3:37])=[C:2]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:3]=3)[N:8]=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 866849816-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline

Product 1

HCID 866849802-(3,5-Dimethylphenyl)-6,7-diisobutylquinolineYield 413.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

6-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline (5.2 g, 15.0 mmol), isobutylboronic acid (6.12 g, 60.0 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.99 g, 2.4 mmol), Pd2(dba)3 (0.549 g, 0.60 mmol), potassium phosphate monohydrate (34.5 g, 150 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, eluting with 2:1 (v/v) hexanes:DCM, to give 2-(3,5-dimethylphenyl)-6,7-diisobutylquinoline (3.43 g, 66%).

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
  6. washeluting with 2:1 (v/v) hexanes

Sources & evidence

ORD record
ord-39b7a24feb88495ab292b3423e8c322c
Source dataset
uspto-grants-2015_12
Patent number
US09217004B2

Reaction notes

Loading…