N-bromobutanimide → HCID 117769989, compound

HRID 1526370Notes

Reaction equation

HRID 1526370 reaction equation
[CH:1]1([CH:4]([N:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:14]#[N:15])[C:7]2=[O:16])[CH3:5])[CH2:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O>CN(C)C=O>[Br:17][C:10]1[C:9]([O:12][CH3:13])=[C:8]([C:14]#[N:15])[C:7](=[O:16])[N:6]([CH:4]([CH:1]2[CH2:3][CH2:2]2)[CH3:5])[CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 117770057HCID 117770057, compound

Product 1

HCID 117769989HCID 117769989, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(1-cyclopropylethyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step A of Example 163 (2.45 g), N-bromosuccinimide (3.00 g) and N,N-dimethylformamide (50 mL) was stirred at 60° C. for 16 hr. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.73 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-198ef4760fff49f6b1005bcbcdc919e2
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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