N-bromobutanimide → HCID 68686099, compound

HRID 2238637Notes

Reaction equation

HRID 2238637 reaction equation
C(O/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH3:13])[N:7]=1)C.BrN1C(=O)CCC1=O.[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][C:26]=1[NH2:31]>O1CCOCC1.O>[CH3:13][S:12][C:8]1[N:7]=[C:6]([C:5]2[N:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([O:23][CH3:22])=[O:32])[C:26]3=[N:31][CH:4]=2)[CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 18506912HCID 18506912, compound

Product 1

HCID 68686099HCID 68686099, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

137.2 mg of the 4-[(E)-2-ethoxyvinyl]-2-(methylthio)pyrimidine [25-2] was dissolved in a mixture solvent of 5 mL of 1,4-dioxane and 2 mL of water, and 124.1 mg of N-bromosuccinimide was added thereto. After stirring at room temperature for 1 hour, 106 mg of the 2-aminonicotinic acid methylester [25-1] was added, and stirred at 85° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative thin layer chromatography, to obtain 106.1 mg of methyl 3-[2-(methylthio)-4-pyrimidinyl]imidazo[1,2-a]pyridine-8-carboxylate [25-3].

Workup

  1. additionwas added
  2. stirringstirred at 85° C. for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1769578a4a444457b1559b73e869bd17
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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