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

HRID 586373ノート

反応式

HRID 586373 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-06c4efba44ac47e58c27ce557ec844a2
出典データセット
uspto-grants-2005_08
特許番号
US06936617B2

反応ノート

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