1,2-Dimethoxyethane → 5-Methyl-2-phenylpyridine

HRID 363183

Reaction equation

HRID 363183 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Ba+2].[OH-].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:9]1([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 5642162-Bromo-5-methylpyridineHCID 6093286Barium hydroxide

Product 1

HCID 474675-Methyl-2-phenylpyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-bromo-5-methylpyridine (2.00 g, 11.63 mmol), phenylboronic acid (1.56 g, 12.79 mmol), barium hydroxide (5.50 g, 17.4 mmol), DME (80 mL) and water (15 mL) was purged with dry argon. Tetrakis(triphenylphosphine)palladium(0) (672 mg, 0.58 mmol) was added, and the resultant solution was stirred at 80° C. for 4 hours. The solvents were evaporated in vacuo, and the residue partitioned between EtOAc and water and acidified with 1M aq. HCl. The aqueous extract was separated, and extracted with EtOAc. The organic extracts were combined, washed with NaHCO3 and 5% aq. Na2S2O3, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by chromatography (Silica gel, CH2Cl2) to afford the title compound.

Workup

  1. customwas purged with dry argon
  2. customThe solvents were evaporated in vacuo
  3. customthe residue partitioned between EtOAc and water
  4. extractionThe aqueous extract
  5. customwas separated
  6. extractionextracted with EtOAc
  7. washwashed with NaHCO3 and 5% aq. Na2S2O3
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent evaporated in vacuo
  11. customThe residue was purified by chromatography (Silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-36559187cfe5434bbbe6d03befe89f64
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Linked notes

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