Pyridine → Ethyl 4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1411138Notes

Reaction equation

HRID 1411138 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][NH:7][C:6](=[O:10])[C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[C:6](=[O:10])[C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 53393185Ethyl 4-Ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 68735913Ethyl 4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 4-ethoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (60 g, 0.284 mol), 4-fluoro phenylboronic acid (120 g, 0.853 mol), Cu(OAc)2 (113 g, 0.568 mol) and pyridine (88 g, 1.137 mol) in DCM (500 mL) was stirred at RT for 4 h open to air. The reaction mixture was filtered and the solids were washed with water. The filtrate was extracted with DCM (2×250 mL). The combined organics were dried over Na2SO4 and concentrated to afford ethyl 4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate. The product was carried forward without further purification. (77 g, 95% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with water
  3. extractionThe filtrate was extracted with DCM (2×250 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b717b0d552de4d11ad7296fb68447fb0
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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