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

HRID 1016642

反応式

HRID 1016642 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.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1.C(=O)([O-])O.[Na+].O>CN(C)C=O>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=3)[N:19]=2)[CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 153482-Amino-5-methylpyridineHCID 692722-Bromo-4'-methylacetophenoneHCID 516892Sodium Bicarbonate

生成物 1

HCID 6677206-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 2-bromo-1-(4-methylphenyl)ethanone (99.3 g, 0.47 mol) in dimethylformamide (250 mL) was added slowly to a solution of 5-methyl-2-pyridinamine (50.4 g, 0.47 mol) in dimethylformamide (250 mL). Sodium hydrogen carbonate (78.3 g, 0.93 mol) was added in portions and the mixture was stirred at room temperature for 15 min., then under reflux for 1.5 h. The mixture was cooled and poured into water (2500 mL). The solid was collected, washed with water (1000 mL) and recrystallised from dimethylformamide (400 mL). The solid was collected and dried in vacuo at 120° C. to give the title compound (89 g, 86%). 1H NMR (360 MHz, DMSO-d6) δ 8.30 (1H, d, J 1.5 Hz), 8.23 (1H, s), 7.84 (2H, d, J 8.0 Hz), 7.47 (1H, d, J 9.2 Hz), 7.25 (2H, d, J 8.0 Hz), 7.09 (1H, dd, J 9.2, 1.5 Hz), 2.33 (3H, s), and 2.28 (3H, s).

後処理

  1. temperatureunder reflux for 1.5 h
  2. temperatureThe mixture was cooled
  3. customThe solid was collected
  4. washwashed with water (1000 mL)
  5. customrecrystallised from dimethylformamide (400 mL)
  6. customThe solid was collected
  7. customdried in vacuo at 120° C.

出典と根拠

ORDレコード
ord-e8d4952219b74732a4bd9df57ceef865
出典データセット
uspto-grants-2002_11
特許番号
US06476045B2

関連ノート

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