Cesium carbonate → 5-(6-chloropyridin-3-yl)-1-ethylpyridin-2(1H)-one

HRID 1925169Notes

Reaction equation

HRID 1925169 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=1.[Cl:11][C:12]1[N:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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>[Cl:11][C:12]1[N:17]=[CH:16][C:15]([C:2]2[CH:3]=[CH:4][C:5](=[O:10])[N:6]([CH2:8][CH3:9])[CH:7]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 38450342-Chloropyridine-5-boronic acidHCID 122105365-Bromo-1-ethylpyridin-2(1H)-one

Product 1

HCID 592332885-(6-chloropyridin-3-yl)-1-ethylpyridin-2(1H)-oneYield 54.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-bromo-1-ethylpyridin-2(1 H)-one (1.9 g, 9.45 mmol), 6-chloropyridin-3-ylboronic acid (1.8 g, 11.46 mmol), Cs2CO3 (9.9 g, 30.37 mmol) and tetrakis(triphenylphosphine)palladium (0) (543 mg, 0.55 mmol) were suspended in dioxane:water (15:1, 20 ml). After degassing, the mixture was heated in a microwave at 140° C. for 30 min. The reaction was then diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness via rotary evaporation. The resulting residue was purified by LCMS to provide the title compound, 5-(6-chloropyridin-3-yl)-1-ethylpyridin-2(1 H)-one (1.2 g, 51% yield).

Workup

  1. customAfter degassing
  2. additionThe reaction was then diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness via rotary evaporation
  7. customThe resulting residue was purified by LCMS

Sources & evidence

ORD record
ord-2be1bd6f38564219b32c7cb50da8b1d3
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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