Methyl iodide → 8-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

HRID 2121484노트

반응식

HRID 2121484 반응식
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=2)[CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=2)[CH:12]=[C:13]([CH2:15][O:16][CH3:24])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 121060838-Benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

생성물 1

HCID 218739748-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under an atmosphere of inert gas, a suspension of 1.2 g of 8-benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridine in 12 ml of dimethylformamide is admixed with 0.36 g of 60% sodium hydride in paraffin, and the mixture is stirred at room temperature for 30 minutes, until the generation of gas has ceased, and then, at room temperature, admixed with 0.56 ml of methyl iodide. After a reaction time of one hour, the mixture is poured into 100 ml of ice-water and extracted three times with in each case 100 ml of ethyl acetate. The organic phases are combined and washed with water. The solvent is removed in vacuo and the oily residue is chromatographed on silica gel (mobile phase: methylene chloridelmethanol=100/1). This gives 0.34 g of the title compound of melting point 107° C. (diethyl ether).

후처리

  1. customat room temperature
  2. extractionextracted three times with in each case 100 ml of ethyl acetate
  3. washwashed with water
  4. customThe solvent is removed in vacuo
  5. customthe oily residue is chromatographed on silica gel (mobile phase: methylene chloridelmethanol=100/1)

출처 및 근거

ORD 기록
ord-81c653e2550948a39c9d0abcfd4ccad9
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696461B2

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