Dimethyl Sulfoxide → 3-(5-Bromo-pyridin-2-yl)-1-methyl-2-oxo-pyrrolidine-3-carboxylic acid ethyl ester

HRID 1425994Notes

Reaction equation

HRID 1425994 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[CH2:9]([O:11][C:12]([CH:14]1[CH2:18][CH2:17][N:16]([CH3:19])[C:15]1=[O:20])=[O:13])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>C(O)(=O)C>[CH2:9]([O:11][C:12]([C:14]1([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:18][CH2:17][N:16]([CH3:19])[C:15]1=[O:20])=[O:13])[CH3:10]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 27831685-Bromo-2-fluoropyridineHCID 12173151Ethyl 1-methyl-2-oxopyrrolidine-3-carboxylate

Product 1

HCID 679978383-(5-Bromo-pyridin-2-yl)-1-methyl-2-oxo-pyrrolidine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-fluoro-pyridine (3.45 g), 1-methyl-2-oxo-pyrrolidine-3-carboxylic acid ethyl ester (5.00 g), cesium carbonate (12.77 g), and dimethyl sulfoxide (10 mL) was stirred at 100° C. overnight. After cooling to room temperature, acetic acid (4.5 mL) was added and the resulting solution was extracted with ethyl acetate. The extract was washed with brine, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel (dichloromethane/ethyl acetate 1:0→1:1) to give the title compound as an oil. Yield: 3.92 g (61% of theory); Mass spectrum (ESI+): m/z=327/329 (Br) [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (dichloromethane/ethyl acetate 1:0→1:1)

Sources & evidence

ORD record
ord-7c17e53cef174e41b9d38e4bb9d09047
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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