N-bromobutanimide → HCID 11241942, compound

HRID 2085902Notes

Reaction equation

HRID 2085902 reaction equation
[CH3:1][O:2][C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([CH3:12])[CH:4]=1.C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:20][C:9]1[N:8]2[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH3:12])=[CH:6][C:7]2=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 112866295-Methoxy-7-methylimidazo[1,2-a]pyridine

Product 1

HCID 11241942HCID 11241942, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-methoxy-7-methylimidazo[1,2-a]pyridine (900 mg, 5.6 mmol) in carbon tetrachloride (100 mL), is added N-bromosuccimide (990 mg, 5.6 mmol). It is stirred at room temperature for 2 h. The reaction solution is then filtered through celite and the filtrate concentrated in vacuo. Ethyl acetate (150 mL) and water are added to the residue. The organic layer is separated and extracted with hydrochloric acid (1N, 3×100). The combined aqueous layer is neutralized with ammonium hydroxide at 0° C. and extracted with dichloromethane (3×200 mL). The combined organic layer is dried over sodium sulfate. The solvent is removed to give 3-bromo-5-methoxy-7-methylimidazo[1,2-a]pyridine (1.1 g, 78%) as a white solid, m.p. 105-106° C.

Workup

  1. filtrationThe reaction solution is then filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionEthyl acetate (150 mL) and water are added to the residue
  4. customThe organic layer is separated
  5. extractionextracted with hydrochloric acid (1N, 3×100)
  6. customis neutralized with ammonium hydroxide at 0° C.
  7. extractionextracted with dichloromethane (3×200 mL)
  8. dry with materialThe combined organic layer is dried over sodium sulfate
  9. customThe solvent is removed

Sources & evidence

ORD record
ord-c0da2c229b1641008519c05c265980f7
Source dataset
uspto-grants-2004_04
Patent number
US06723332B2

Reaction notes

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