Methyl 5-(4-fluorophenyl)-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylate → Methyl 5-(4-fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1909156Notes

Reaction equation

HRID 1909156 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[N:12]([CH:15]([C:17](=[O:19])[CH3:18])[CH3:16])[CH:11]=[C:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:24][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[N:12]([CH:15]([C:17]([OH:19])([CH3:24])[CH3:18])[CH3:16])[CH:11]=[C:10]([C:20]([O:22][CH3:23])=[O:21])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67338493Methyl 5-(4-fluorophenyl)-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 67338292Methyl 5-(4-fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(4-fluorophenyl)-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylate (11.1 g, 35.0 mmol) in tetrahydrofuran (175 mL) at 0° C. was added methylmagnesium bromide (3.0 M in THF; 14.0 mL, 42.0 mmol). After 20 min, the mixture was quenched with saturated aqueous sodium bicarbonate. The mixture was cooled to ambient temperature and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→80% dichloromethane/ethyl acetate) gave the title compound. MS 334.2 (M+1).

Workup

  1. customthe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→80% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-aaa4543d43db47589ffd7747889662f2
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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