N-bromobutanimide → Ethyl 3-bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1971625Notes

Reaction equation

HRID 1971625 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]2[CH:23]=1)=[O:13])[CH3:10]>C(#N)C>[CH2:9]([O:11][C:12]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]2[C:23]=1[Br:1])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 821015Ethyl 5-methylimidazo[1,2-a]pyridine-2-carboxylate2×

Product 1

HCID 58379339Ethyl 3-bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (0.288 g, 0.00162 mol) was added in portions to a solution of 5-methylimidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (compound n, 0.3 g, 0.001 mol) in acetonitrile (7 mL) at 0° C. The reaction was stirred at 0° C. for 15 minutes. The solvent removed then water (10 mL) and ethyl acetate (10 mL) was added. The layers were separated and the organic layer dried (magnesium sulfate) then removed. The crude product was chromatographed using 30% ethyl acetate/hexanes to give 3-Bromo-5-methyl-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester as a light brown solid. Rf 0.35, 80% ethyl acetate/hexanes; MS m/z 284 (M+H).

Workup

  1. customThe solvent removed
  2. additionwater (10 mL) and ethyl acetate (10 mL) was added
  3. customThe layers were separated
  4. dry with materialthe organic layer dried (magnesium sulfate)
  5. customthen removed
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-006b5434b9be483dbf2950976cf8a57c
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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