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

HRID 586373노트

반응식

HRID 586373 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-06c4efba44ac47e58c27ce557ec844a2
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936617B2

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