(2-Methylpropyl)boronic acid → HCID 71236339, compound

HRID 713556Notes

Reaction equation

HRID 713556 reaction equation
Br[C:2]1[C:3]([CH3:21])=[CH:4][C:5]([C:8]2[C:13]3[O:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:22](B(O)O)[CH:23]([CH3:25])[CH3:24].O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH:11]1[C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:8]([C:5]2[CH:4]=[C:3]([CH3:21])[C:2]([CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:7][N:6]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 3

HCID 2734395(2-Methylpropyl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 71007915HCID 71007915, compound

Product 1

HCID 71236339HCID 71236339, compoundYield 74.5%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5-Bromo-2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine (13.0 g, 38.3 mmol), isobutylboronic acid (11.7 g, 115 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.63 g, 1.53 mmol) and potassium phosphate monohydrate (22.1 g, 96 mmol) were mixed in water (10 mL) and toluene (210 mL). The system was degassed for 20 min. with nitrogen and Pd2(dba)3 (0.35 g, 0.38 mmol) was then added and the system was refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a small plug of silica gel and eluted with dicloromethane. The filtrated was concentrated and then crystallized from hexane to give 2-(dibenzo[b,d]furan-4-yl)-5-isobutyl-4-methylpyridine (9.0 g, 74%).

Workup

  1. additionwas then added
  2. temperaturethe system was refluxed overnight
  3. filtrationthe reaction mixture was filtered through a small plug of silica gel
  4. washeluted with dicloromethane
  5. concentrationThe filtrated was concentrated
  6. customcrystallized from hexane

Sources & evidence

ORD record
ord-3680e06fe5ed4ef9ab5efa6863fd0c6e
Source dataset
uspto-grants-2015_11
Patent number
US09184397B2

Reaction notes

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