Methyl iodide → 2-Phenoxy-3-[3-(3-methoxypyridin-4-yl)propoxy]pyridine

HRID 1841566노트

반응식

HRID 1841566 반응식
[H-].[Na+].[O:3]([C:10]1[C:15]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[OH:26])=[CH:14][CH:13]=[CH:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CI.[C:29](OCC)(=O)C>CN(C=O)C>[O:3]([C:10]1[C:15]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[O:26][CH3:29])=[CH:14][CH:13]=[CH:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 98836252-Phenoxy-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine

생성물 1

HCID 235062462-Phenoxy-3-[3-(3-methoxypyridin-4-yl)propoxy]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (60% in mineral oil, 0.04 g, 1.0 mmol) is suspended in DMF (10 ml), and thereto is added 2-phenoxy-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine (0.20 g, 0.62 mmol) obtained in Example 30 at room temperature, and the mixture is stirred for 30 minutes. To the mixture is added methyl iodide (0.06 ml, 1.0 mmol) under ice-cooling, and the mixture is stirred for 10 minutes. To the reaction solution is added ethyl acetate (50 ml), and the mixture is washed with a saturated brine (30 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol), and recrystallized from isopropyl ether to give the title compound (0.09 g) as colorless crystals, m.p. 101-102° C.

후처리

  1. temperaturecooling
  2. stirringthe mixture is stirred for 10 minutes
  3. washthe mixture is washed with a saturated brine (30 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)
  7. customrecrystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-f7d1fb92e8f849778d6a872f41c22406
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683186B2

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