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

HRID 500750

반응식

HRID 500750 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 70.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 2-bromo-1-p-tolyl-ethanone (500 mg, 2.3 mmol) in dimethylformamide (2 mL) was added slowly to a solution of 5-methyl-pyridin-2-yl-amine (249 mg, 2.3 mmol) in dimethylformamide (2 mL). NaHCO3 (386 mg, 4.6 mmol) was added in portions and the mixture was stirred at room temperature for 15 minutes, then at reflux for 1.5 hours. The mixture was cooled and poured into water (5 mL). The solid was collected, washed with water (2 mL) and recrystallized from dimethylformamide (5 mL) to yield the desired product 6-methyl-2-p-tolyl-imidazo[1,2-a]pyridine (360 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H), 2.32 (s, 3H), 7.08 (d, 1H), 7.21 (d, 2H), 7.46 (d, 1H), 7.83 (d, 2H), 8.24 (s, 1H), 8.29 (s, 1H); ESI-MS (MH+), 223.

후처리

  1. temperatureat reflux for 1.5 hours
  2. temperatureThe mixture was cooled
  3. customThe solid was collected
  4. washwashed with water (2 mL)
  5. customrecrystallized from dimethylformamide (5 mL)

출처 및 근거

ORD 기록
ord-6133d36d4b3b41f0bce50c83586cf962
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772248B2

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