Sodium Iodide → Ethyl 5-Chloropyridine-2-carboxylate

HRID 2417495Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[I-].[Na+].[C:11](Cl)(=[O:13])C.C1(P([C:28]2[CH:33]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=[O:42]>C(#N)C.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]([O:13][CH2:33][CH3:28])=[O:42])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.2 g (8.2 mmol) of 2,5-dichloropyridine was dissolved in 50 ml of acetonitrile. 1.46 g (9.7 mmol) of sodium iodide and 0.7 ml (9.7 mmol) of acetyl chloride were added to the obtained solution, and they were stirred at 50° C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 15 ml of DMF. 182 mg (0.8 mmol) of palladium acetate, 147 mg (0.56 mmol) of triphenylphosphine, 2.3 ml of ethanol and 1.3 ml (9.7 mmol) of triethylamine were added to the obtained solution, and they were stirred in the presence of carbon monoxide at 70° C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

customwas purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-36e474b983a84ee6bceb2d633a26ca68
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825191B2

Reaction notes

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