2-Aminopyridine → 2-Methylimidazo[1,2-a]pyridine

HRID 37213

Reaction equation

HRID 37213 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1C(CC2C=CC(C3C(C(OC(C)(C)C)=O)=CC=CC=3)=CC=2)=C2CCCCN2N=1)[CH2:9]CC.BrCC(=O)C>CC(C)=O>[CH3:12][C:8]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:9]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 11715BromoacetoneHCID 190324691,1-Dimethylethyl 4'-[(2-butyl 4,5,6,7-tetrahydro pyrazolo(1,5-a)pyridin-3-yl)methyl](1,1'-biphenyl)2-carboxylate

Product 1

HCID 1367422-Methylimidazo[1,2-a]pyridineYield 245.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 5 g of 2-amino pyridine and 250 ml of acetone were added at ambient temperature to a mixture of 7.25 g of 1 bromo 2-propanone and 20 ml of acetone and the mixture was refluxed for 30 minutes. Using the procedure of Stage C of Example 22, 5.3 g of the expected product were obtained in the form of an orange oil.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes

Sources & evidence

ORD record
ord-a3c2d8350f0a4600b896fc04423ca462
Source dataset
uspto-grants-1995_05
Patent number
US05420138

Linked notes

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