2,3-Dimethyl 2,3-pyridinedicarboxylate → Methyl 2-(2-(4-fluorophenyl)acetyl)nicotinate

HRID 1259294

Reaction equation

HRID 1259294 reaction equation
CO[C:3]([C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].[F:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][Mg]Cl)=[CH:18][CH:17]=1>O1CCCC1>[F:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][C:3]([C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[O:4])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 178505759HCID 178505759, compound

Product 1

HCID 69046764Methyl 2-(2-(4-fluorophenyl)acetyl)nicotinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethylpyridine-2,3-dicarboxylate (1.0 g, 5.1 mmol) in tetrahydrofuran (50 ml) was added (4-fluorobenzyl)magnesium chloride (0.25 M in tetrahydrofuran, 20 ml, 5.1 mmol) through a syringe at −78° C. The reaction mixture was stirred at the same temperature for 30 minutes and was quenched with addition of water. After warming up to room temperature, the reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (15% ethyl acetate in hexane) to give the title compound. MS (DCI/NH3) m/z 274 (M+H)+.

Workup

  1. customwas quenched with addition of water
  2. customthe reaction mixture was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-44aaedc0e1204c75928e98200ce08149
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Linked notes

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