(2-Methylpropyl)boronic acid → 2-(3,5-Dimethylphenyl)-5-isobutylquinoline

HRID 2275972Notes

Reaction equation

HRID 2275972 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)=[N:7]2.[CH2:20](B(O)O)[CH:21]([CH3:23])[CH3:22].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:19][C:14]1[CH:13]=[C:12]([C:6]2[CH:5]=[CH:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[CH2:20][CH:21]([CH3:23])[CH3:22])[N:7]=2)[CH:17]=[C:16]([CH3:18])[CH:15]=1

Participants

6

Reactant 4

HCID 2734395(2-Methylpropyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 681069905-Chloro-2-(3,5-dimethylphenyl)quinoline

Product 1

HCID 681071002-(3,5-Dimethylphenyl)-5-isobutylquinolineYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Chloro-2-(3,5-dimethylphenyl)quinoline (4.3 g, 16.06 mmol), isobutylboronic acid (3.2 g, 31.4 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.538 g, 1.31 mmol), and potassium phosphate monohydrate (18.3 g, 79 mmol) were mixed in 114 mL of toluene. The system was degassed for 20 minutes. Pd2(dba)3 was then added and the system was refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with dichloromethane. The product was further purified by a Kugelrohr distillation and then further purified by column chromatography using 5% ethyl acetate in hexanes. This was followed by another Kugelrohr distillation to give 3.2 g (72% yield) of product.

Workup

  1. customThe system was degassed for 20 minutes
  2. additionPd2(dba)3 was then added
  3. temperaturethe system was refluxed overnight
  4. filtrationthe reaction mixture was filtered through a Celite® plug
  5. washeluted with dichloromethane
  6. distillationThe product was further purified by a Kugelrohr distillation
  7. customfurther purified by column chromatography
  8. distillationThis was followed by another Kugelrohr distillation

Sources & evidence

ORD record
ord-38d98de5a8a04c2fa0e9d440a250565c
Source dataset
uspto-grants-2015_09
Patent number
US09130177B2

Reaction notes

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