Sodium Iodide → 2-(4-Chlorophenyl)imidazo(1,2-a)pyridine-3-acetonitrile

HRID 455131Notes

Reaction equation

HRID 455131 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.[C-:20]#[N:21].[Na+].[Na+].[I-]>C(#N)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[N:6]=[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]3[C:4]=2[CH2:3][C:20]#[N:21])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 670287193-(Chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 872822-(4-Chlorophenyl)imidazo(1,2-a)pyridine-3-acetonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30.0 g of molecular sieves were activated under vacuum, at 100° C., for 1 h. 5.00 g of 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride (15.94 mmol, 1 eq), 9.38 g of NaCN (191.3 mmol, 12 eq), 428 mg of Bu4NCN (1.59 mmol, 0.1 eq), 9.56 g of NaI (63.77 mmol, 4 eq) and 150 mL of ACN were added. The mixture were stirred at RT, O/N. Sieves were filtered and washed with EtOAc. The filtrate was washed twice with NaHCO3, dried on MgSO4, filtered and concentrated to give 4.95 g of crude. It was purified by silica gel chromatography (MeOH/CH2Cl2, 0 to 5%) and gave two batches: batch #01 (very pure)=3.90 g, batch #02 (some impurities) was purified on activated carbon to give 0.90 g. Total yield=82%. m/e+=268 (M+H+).

Workup

  1. filtrationSieves were filtered
  2. washwashed with EtOAc
  3. washThe filtrate was washed twice with NaHCO3
  4. customdried on MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 4.95 g of crude
  8. customIt was purified by silica gel chromatography (MeOH/CH2Cl2, 0 to 5%)
  9. customgave two batches
  10. custombatch #01 (very pure)=3.90 g, batch #02 (some impurities) was purified on activated carbon
  11. customto give 0.90 g

Sources & evidence

ORD record
ord-b193694e7632485b8c998c3c7d3f06ed
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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