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

HRID 455016

反応式

HRID 455016 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
93 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b6886f612bfc400186c581140ec85fad
出典データセット
uspto-grants-2013_07
特許番号
US08497278B2

関連ノート

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