2-Bromobutane → HCID 89580547, compound

HRID 1479758Notes

Reaction equation

HRID 1479758 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH:13]([CH2:15][CH3:16])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:13]([N:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]1=[O:1])([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 65542-BromobutaneHCID 10796Cesium carbonateHCID 178498433HCID 178498433, compound

Product 1

HCID 89580547HCID 89580547, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-hydroxyisonicotinate (306 mg, 2 mmol) in N,N-dimethylformamide (20 mL) was added 2-bromobutane (330 mg, 2.4 mmol) and cesium carbonate (652 mg, 2 mmol), then stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography with dichloromethane/methanol=40:1 to give methyl 1-sec-butyl-2-oxo-1,2-dihydropyridine-4-carboxylate (334 mg, 80%). LRMS (M+H+) m/z: calcd 209.11. found 209.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography with dichloromethane/methanol=40:1

Sources & evidence

ORD record
ord-619ae558c56746f7806eb69d3fff205f
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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