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

HRID 1478678Notes

Reaction equation

HRID 1478678 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[Br:16][C:8]1[N:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]2=[N:10][C:9]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

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

Product 1

HCID 58379339Ethyl 3-bromo-5-methylimidazo[1,2-a]pyridine-2-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of ethyl 5-methylimidazo[1,2-a]pyridine-2-carboxylate (5.0 g, 25 mmol) in acetonitrile (94 mL) was treated with N-bromosuccinimide (4.8 g, 27 mmol) in acetonitrile (47 mL) dropwise and stirred at 20° C. for 30 min. The reaction mixture was concentrated, diluted with dichloromethane (200 mL), and washed with saturated sodium bicarbonate (150 mL) and brine (50 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated to a crude solid. Purification by flash column chromatography gave the desired product (4.0 g, 58%). LCMS for C11H12BrN2O2 (M+H)+: m/z=282.9, 284.9.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with dichloromethane (200 mL)
  3. washwashed with saturated sodium bicarbonate (150 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude solid
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-7659a292fd2846178eb9a0ec7e919f75
Source dataset
uspto-grants-2016_08
Patent number
US09403847B2

Reaction notes

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