Potassium Carbonate → Ethyl 5-fluoropyridine-2-carboxylate

HRID 2080695Notes

Reaction equation

[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[C:7]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:8]=1.Cl[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][N:38]=1.[C]=O>CN(C)C=O.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:43][C:40]1[CH:41]=[CH:42][C:37]([C:1]([O:2][CH2:7][CH3:8])=[O:4])=[N:38][CH:39]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1.57 g of potassium carbonate, 0.34 g of 1,3-bis(diphenylphosphino)propane and 0.17 g of palladium acetate were added to a solution of 1 g of 2-chloro-5-fluoropyridine in 8 ml of dimethylformamide and 8 ml of ethanol, and stirred in a carbon monoxide atmosphere under heat at 90° C. for 2 hours. The reaction liquid was filtered, the filtrate was extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 0.97 g of the entitled compound as a white crystal.

Workup

customThe reaction liquid
filtrationwas filtered
extractionthe filtrate was extracted with chloroform
washthe organic layer was washed with saturated saline water
customAfter dried
customthe solvent was evaporated away under reduced pressure
customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-4eaa7147ba2940888eecaf175ea07b14
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932394B2

Reaction notes

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