2-Bromopyridine → 6'-Methoxy-2,3'-bipyridyl

HRID 2356926Notes

Reaction equation

HRID 2356926 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][N:8]=1

Participants

9

Reactant 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 108993656'-Methoxy-2,3'-bipyridylYield 118.8%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Methoxy-3-pyridylboronic acid (105 g), 2-bromopyridine (90 g), palladium acetate (3.21 g), triphenylphosphine (15 g), potassium carbonate (237 g), 1,2-dimethoxyethane (900 mL) and water (900 mL) were heated under reflux for 5 hours and 40 minutes under stirring. After cooling the reaction solution, ethyl acetate (1 L) was added thereto to extract. The organic layer was washed with 1 L of 10% aqueous solution of ammonium chloride, 1 L of 10% aqueous ammonia and 1 L of 10% saline, and then evaporated, to give 126 g (87%) of the title compound.

Workup

  1. temperatureunder reflux for 5 hours and 40 minutes
  2. additionwas added
  3. extractionto extract
  4. washThe organic layer was washed with 1 L of 10% aqueous solution of ammonium chloride, 1 L of 10% aqueous ammonia and 1 L of 10% saline
  5. customevaporated

Sources & evidence

ORD record
ord-3f866464a4ef4b41b70d74e836337eb7
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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