Imidazole → 3-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine

HRID 455017Notes

Reaction equation

HRID 455017 reaction equation
Cl.Cl[CH2:3][C:4]1[N:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C([O-])(O)=O.[Na+]>C(C#N)(C)=O>[N:21]1([CH2:3][C:4]2[N:8]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]3=[N:6][C:5]=2[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 516892Sodium BicarbonateHCID 670287243-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride (0.10 mmol), 1H-imidazole (0.20 mmol, 2.0 eq) in AcCN (1 ml) was heated at 65° C. overnight. The mixture was basified with sat. NaHCO3 (5 ml), extracted with ethyl acetate or CH2Cl2 (2×5 ml). The combined organic solution was dried with Na2SO4, evaporated under vacuum. The product was purified by silica gel column chromatography (12 g silica gel RediSep column, eluted first with 10% ethyl acetate in hexane, then 20-50% acetone in hexane), to afford the product as a white solid. The product shows up as violet spot on TLC plate under UV light. m/e+ 303.4 for C19H19N4 (M+H)+; 1H-NMR (400 MHz, CDCl3, δ) 7.60-7.50 (m, 5H), 7.26 (d, J=8.065 Hz, 2H), 7.11 (m, 2H), 6.883 (s, 1H), 5.51 (s, 2H), 2.39 (s, 3H), 2.285 (s, 3H) ppm; 13C-NMR (100 MHz, CDCl3, δ), 146.681, 144.944, 138.582, 136.512, 130.787, 130.484, 129.832, 128.937, 128.330, 123.341, 120.710, 118.845, 117.396, 112.315, 40.969, 21.512, 18.608 ppm.

Workup

  1. extractionextracted with ethyl acetate or CH2Cl2 (2×5 ml)
  2. dry with materialThe combined organic solution was dried with Na2SO4
  3. customevaporated under vacuum
  4. customThe product was purified by silica gel column chromatography (12 g silica gel RediSep column
  5. washeluted first with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6ecef95fb9fa4ea8bb328056ffcfc50a
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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