Chlorosuccinimide → 3-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

HRID 1798706Notes

Reaction equation

HRID 1798706 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][CH2:10][C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[CH:19]=1>C(Cl)Cl>[Cl:1][C:19]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[CH2:10][Cl:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridine

Product 1

HCID 595801663-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Chloro succinimide (329 g, 2.46 mmol) was added to a solution of 2-(chloromethyl)imidazo[1,2-a]pyridine (450 mg, 2.2 mmol) in DCM (15 ml) at RT under an atmosphere of nitrogen. Stirring was continued for 2 h (reaction was monitored by TLC) upon which the reaction mixture was diluted with DCM and washed with water and brine solution. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using 10% ethyl acetate in n-hexane and silica gel (230-400 mesh) to afford 3-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (400 mg, 76%) as Off-white solid. 1H NMR: 200 MHz, CDCl3: δ 8.4 (d, 1H), 7.7 (d, 1H), 7.5 (t, 1H), 7.1 (t, 1H), 4.85 (s, 2H). MS: [M+H]+: m/z=201.8. HPLC: (98.3%, Condition-A).

Workup

  1. custom(reaction was monitored by TLC) upon which the reaction mixture
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-226fcdff754340c88de6574d7d5f3b79
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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