Sodium hydride → 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

HRID 586373Notes

Reaction equation

HRID 586373 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)[CH:8]=[CH:9][CH:10]=1)#[N:4].Cl[CH2:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]2[C:26]=1[CH2:27][CH2:28][CH3:29]>CN(C=O)C>[CH2:27]([C:26]1[N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19][C:18]=1[CH2:17][N:15]1[CH:14]=[CH:13][N:12]=[C:11]1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]#[N:4])[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 223350602-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridineHCID 223350823-(1H-Imidazol-2-yl)benzonitrile

Product 1

HCID 208256803-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (13.5 mg of 60% wt., 0.34 mmol) is added to a solution of 3-cyano-(1H-imidazol-2-yl)benzene (57.2 mg, 0.34 mmol) in anhydrous DMF (3.5 mL). After 15 minutes, 2-chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine (70.5 mg, 0.34 mmol) is added and the reaction mixture is stirred at ambient temperature for 18 hours. Concentration at reduced pressure followed by purification by chromatography on silica gel (5% MeOH/CHCl3) provides 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile as a light yellow solid. TLC (5% MeOH/CHCl3) Rf=0.50. 1H NMR (CDCl3): 8.13, s (1H); 8.07, d (1H); 7.90, d (1H); 7.71, d (1H); 7.60, d (1H); 7.58, d (1H); 7.20, dd (1H); 7.14, bs (2H); 6.85, t (1H); 5.32, s (2H); 2.70, t (2H); 1.50, p (2H), 0.90, t (3H). LRMS m/z (M+1) 342.30.

Workup

  1. concentrationConcentration at reduced pressure
  2. customfollowed by purification by chromatography on silica gel (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-06c4efba44ac47e58c27ce557ec844a2
Source dataset
uspto-grants-2005_08
Patent number
US06936617B2

Reaction notes

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