Diethyl Ether → 6-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine

HRID 455016노트

반응식

HRID 455016 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]1(C)[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][NH:14]1.C([O-])([O-])=O.[K+].[K+].CCOCC>CCO>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]2[N:14]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=3)[N:12]=2)[CH:15]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 692722-Bromo-4'-methylacetophenoneHCID 866551152-Amino-5-methyl picoline

생성물 1

HCID 6677206-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine수율 66.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
93 °C

실험 절차

A mixture of 2-bromo-4′-methylacetophenone (90% pure, 10.21 g, 43.11 mmol), 2-amino-5-methyl picoline (4.66 g, 43.11 mmol) and K2CO3 (6.6 g, 47.75 mmol) in absolute EtOH (70 ml) was heated at 93° C. overnight. After cooled to 40° C., ether (100 mL) was added. The mixture was stirred for 30 minutes and cooled by ice-water bath. After removal of solvent through filtration, the solid was stirred with water (50 ml) for 30 minutes and filtered, rinsed with water and dried under vacuum at 80° C. for 2 hr to give 6.33 g of white solid (66.1% yield). m/e+ 223.4 for C15H15N2 (M+H)+; 1H-NMR (400 MHz, CDCl3, δ) 7.84 (m, 3H), 7.71 (d, J=9.531 Hz, 1), 7.51 (d, J=9.165 Hz, 1H), 7.24 (m, 2H), 7.00 (m, 1), 2.38 (s, 3H), 2.29 (d, J=6.23 Hz, 3H) ppm. 13C-NMR (100 MHz, CDCl3 δ) 145.065, 144.444, 137.991, 130.696, 130.635, 129.642, 129.483, 128.391, 128.262, 126.018, 123.652, 122.476, 116.486, 107.857, 21.520, 18.259 ppm.

후처리

  1. temperatureAfter cooled to 40° C.
  2. temperaturecooled by ice-water bath
  3. customAfter removal of solvent
  4. filtrationthrough filtration
  5. stirringthe solid was stirred with water (50 ml) for 30 minutes
  6. filtrationfiltered
  7. washrinsed with water
  8. customdried under vacuum at 80° C. for 2 hr

출처 및 근거

ORD 기록
ord-b6886f612bfc400186c581140ec85fad
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497278B2

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