Ethanol → Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

HRID 706752Notes

Reaction equation

HRID 706752 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH:10]([CH:16]=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(O)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][N:8]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 706222-Amino-5-bromopyridineHCID 118030Ethyl (chloroformyl)acetate

Product 1

HCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylateYield 30%

Conditions

Temperature
75 °C

Procedure

A mixture of 5-bromopyridin-2-amine (5.22 g, 30.2 mmol) and ethyl 2-chloro-3-oxopropanoate (5.00 g, 33.2 mmol) (Toronto Research Chemicals; 5% solution on benzene) was stirred in ethanol (151 mL, 30.2 mmol) under nitrogen. The mixture was heated to 75° C. for 4 hours and then at ambient temperature for 2 days. The solvent was removed under vacuum to give a solid residue which was purified by silica gel chromatography, eluting with hexane/ethyl acetate (6:4 to 4:6) to give the desired product as a solid (2.40 g; 30%).

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a solid residue which
  3. customwas purified by silica gel chromatography
  4. washeluting with hexane/ethyl acetate (6:4 to 4:6)

Sources & evidence

ORD record
ord-600e6bdc5bb64f2db0331120e01eb084
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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