Biphenyl-2-boronic acid → HCID 59575353, compound

HRID 1468595Notes

Reaction equation

HRID 1468595 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[C:10]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11](B(O)O)=[CH:12][CH:13]=[CH:14][CH:15]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O.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(C)C=CC=CC=1>[C:10]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

8

Reactant 4

HCID 4589187Biphenyl-2-boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 226385104-Chloro-2-methoxypyridine

Product 1

HCID 59575353HCID 59575353, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A nitrogen flushed mixture of 4-chloro-2-methoxypyridine (3.0 g, 21.03 mmol), 2-biphenylboronic acid 5.0 g, 25.23 mmol), Pd2(dba)3 (381 mg, 0.414 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (681 mg, 1.66 mmol), toluene (250 mL) and a slurry of K3PO4.H2O (14.57 g, 63.09 mmol) in water (25 mL) were refluxed for 18 h. After the mixture cooled to room temperature the organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by flash chromatography on silica (hexane:ethyl acetate) and recrystallized from ethyl acetate to give 4-(biphenyl-2-yl)-2-methoxypyridine (4.2 g, 76.5%).

Workup

  1. customA nitrogen flushed
  2. dry with materialwas dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography on silica (hexane:ethyl acetate)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-530a95ceab3e49068b9bcf2a6758864b
Source dataset
uspto-grants-2015_04
Patent number
US09005771B2

Reaction notes

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