N-bromobutanimide → HCID 58459174, compound

HRID 2036560Notes

Reaction equation

HRID 2036560 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH2:11][Cl:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O>C(#N)C>[Br:13][C:8]1[N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]2=[N:10][C:9]=1[CH2:11][Cl:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 573552298-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 58459174HCID 58459174, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (8.5 ml) was added to 8-chloro-2-(chloromethyl)imidazo[1,2-a]-pyridine (341 mg, 1.7 mmol). N-bromosuccinimide (302 mg, 1.7 mL) was added and the mixture was stirred at rt until complete. The reaction mixture was partitioned with EtOAc and satd. aq. NaHCO3 solution. The organic layer was dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was taken up in DCM and purified by chromatography on a 23 g silica gel column using 0 to 70% gradient of EtOAc in hexane. The desired fractions were combined and concentrated under reduced pressure to give 3-bromo-8-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine as a white crystalline solid.

Workup

  1. customThe reaction mixture was partitioned with EtOAc
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified by chromatography on a 23 g silica gel column
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1db06fb30cba41d0b17537fe0ff298fe
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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