Potassium Iodide → Ethyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

HRID 2184304노트

반응식

HRID 2184304 반응식
[NH2:1][C:2]1[C:3]2[N:4]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH2:22]Cl)[CH3:19].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)=O>[CH3:16][C:14]1[N:15]=[C:3]2[C:2]([NH:1][CH2:22][C:21]3[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:20]=3[CH2:18][CH3:19])=[CH:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][N:4]2[C:13]=1[CH3:17]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 9942738Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateHCID 121489182-Ethyl-6-methylbenzyl chloride

생성물 1

HCID 11003040Ethyl 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate수율 10.9%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Ethyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (0.7 g, 3.0 mmol), 2-ethyl-6-methylbenzylchloride (0.5 g, 3.0 mmol), sodium carbonate (0.64 g, 6.0 mmol) and a catalytic amount of potassium iodide were added to acetone (50 ml) and were refluxed for 20 h. Following filtration, the acetone was evaporated under reduced pressure to give an oil. The oily product was purified by column chromatography on silica gel using diethyl ether:petroleum ether (1:1) as eluent to give 0.12 g (9%) of the title product. 1H-NMR (500 MHz, CDCl3): δ 1.25 (t, 3H), 1.5 (t, 3H), 2.35 (s, 3H), 2.42 (s, 3H), 2.44 (s, 3H), 2.75 (q, 2H), 4.45-4.5 (m, 4H), 4.9 (bs, 1H), 6.8 (s, 1H), 7.05-7.2 (m, 3H), 8.1 (s, 1H)

후처리

  1. temperaturewere refluxed for 20 h
  2. filtrationfiltration
  3. customthe acetone was evaporated under reduced pressure
  4. customto give an oil
  5. customThe oily product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-65c306a5f6a84a2fa1e936780ab6ab8a
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900324B2

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