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

HRID 455017노트

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HRID 455017 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 694302-Oxopropiononitrile용매

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온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ecef95fb9fa4ea8bb328056ffcfc50a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497278B2

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