Benzyl Bromide → 1-Benzyl-3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester

HRID 919781Notes

Reaction equation

HRID 919781 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8](=[O:13])[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Li+].[Br-].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8](=[O:13])[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 82050Lithium BromideHCID 19349114Ethyl 6-hydroxy-3-methylpicolinate

Product 1

HCID 682973241-Benzyl-3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl esterYield 45.9%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester (230 mg, 1.27 mmol), toluene (6.4 mL) and water (0.064 mL). K2CO3 (351 mg, 2.54 mmol), LiBr (221 mg, 2.54 mmol), tetrabutylammonium bromide (41 mg, 0.127 mmol), and benzyl bromide (0.23 mL, 1.91 mmol) were added, and the resulting suspension was heated at 80° C. for 40 min. The mixture was allowed to come to r.t., diluted with CH2Cl2, and filtered. The filtrate was concentrated in vacuo, and the residue was chromatographed (0-10% MeOH/CH2Cl2) to give 158 mg of the title compound as a viscous oil. MS: (+) m/z 272.31 (M+1).

Workup

  1. customto come to r.t.
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was chromatographed (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0e639ebc31d1452994e3878f46301d42
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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