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

HRID 1016642노트

반응식

HRID 1016642 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-e8d4952219b74732a4bd9df57ceef865
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06476045B2

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