Cesium carbonate → HCID 21083626, compound

HRID 347702Notes

Reaction equation

HRID 347702 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.Cl[C:10]1[C:15]([C:16]#[N:17])=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([C:10]2[C:15]([C:16]#[N:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 810792-ChloronicotinonitrileHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 21083626HCID 21083626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To 5-bromo-2-pyridone (1.0 g) and 2-chloro-3-cyanopyridine (1.0 g) in dry N,N-dimethylformamide (20 ml) was added caesium carbonate (2.73 g), and the mixture heated at 75° C. under a nitrogen atmosphere for 24 h. The solvent was removed in vacuo from the mixture and the residue partitioned between ethyl acetate and water. The organic layer was evaporated and the residue purified by chromatography (silica gel, 0 to 4% MeOH/CH2Cl2) to give the title compound, crystallised from diethyl ether/isohexane: 1H NMR (400 MHz, CDCl3) δ 8.81 (1H, dd, J 2.0, 5.1), 8.17 (1H, dd, J 1.8, 7.6), 7.67 (1H, d, J 2.7), 7.56 (1H, dd, J 4.9, 7.6), 7.49 (1H, dd, J 2.5, 10.0), 6.62 (1H, d, J 9.8); MS (ES+) m/z 276 and 278 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo from the mixture
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was evaporated
  4. customthe residue purified by chromatography (silica gel, 0 to 4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ec7ab0fa7c6f4b8e805969f52890ee29
Source dataset
uspto-grants-2007_02
Patent number
US07176203B2

Reaction notes

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