Triethylamine → 3-(2-pyridyl)-5-phenyl-2(1H)-pyridone

HRID 497808Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([O:14]C)=[N:9][CH:10]=[C:11](Br)[CH:12]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8](=[O:14])[NH:9][CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 11.0 g of 3-(2-pyridyl)-5-bromo-2-methoxypyridine, 0.9 g of phenylboronic acid, 0.3 g of dichlorobistriphenylphosphine palladium and 2 ml of triethylamine was stirred at 120° C. for 1.5 hours in 30 ml of xylene in nitrogen atomosphere. The mixture was returned to room temperature, diluted with ethyl acetate, washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was incorporated with 47% hydrobromic acid and heated at 70° C. for 1 hour. The reaction solution was ice-cooled, diluted with water, and neutralized with potassium carbonate. The resulting precipitates were collected by filtration, washed with water and ether, and then air-dried, to give 0.5 g of the title compound as a pale yellow powder.

Workup

customwas returned to room temperature
washwashed with water and brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
temperaturecooled
additiondiluted with water
customThe resulting precipitates
filtrationwere collected by filtration
washwashed with water and ether
customair-dried

Sources & evidence

ORD record: ord-37dd760c7ce44807ac40783d2f848ce3
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949571B2

Reaction notes

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