Acetonitrile → HCID 117902772, compound

HRID 1772171Notes

Reaction equation

HRID 1772171 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[N:5]2[CH:11]=1.[I:12]N1C(=O)CCC1=O.C(#N)C>C(Cl)Cl>[I:12][C:11]1[N:5]2[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]2=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 120273N-IodosuccinimideHCID 1386822,5-Dimethylimidazo(1,2-a)pyridine

Product 1

HCID 117902772HCID 117902772, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,5-dimethylimidazo[1,2-a]pyridine (0.5 g, 3.4 mmol), N-iodosuccinimide (770 mg, 3.4 mmol) and ACN (5 ml) is stirred at RT for 45 minutes. The mixture is diluted with DCM and extracted with an aqueous solution sodium thiosulfate. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 775 mg (83%). HPLC-MS: M+H=273; tR=1.02 min (METHOD—1).

Workup

  1. extractionextracted with an aqueous solution sodium thiosulfate
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-039d71eed34f48048ad1f5b66bb0b01a
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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