Methyl iodide → N-(6-ethyl-3-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 900962노트

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HRID 900962 반응식
[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1)[CH3:2].[C:16]([Li])(C)(C)C.CI>C(OCC)C.O>[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]([CH3:16])=[CH:5][CH:4]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 45094816N-(6-ethyl-pyridin-2-yl)-2,2-dimethyl-propionamideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 45095400N-(6-ethyl-3-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

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온도
-20 °C

실험 절차

A solution of N-(6-ethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (24.0 g, 0.116 mol) in diethyl ether (600 mL, 0.2 M) is cooled to −78° C. and treated with tert-butyllithium (144 mL 1.7 M in pentane). After the addition is complete the solution is warmed to −20° C. for 2 h, treated with a solution of methyliodide (23 mL, 0.372 mol) in diethylether (10 mL) and warmed to room temperature. After stirring overnight the reaction is diluted with water, extracted with diethyl ether and dried over MgSO4. The resulting solution is filtered through a short pad of silica gel, concentrated and recrystallized from heptane to give N-(6-ethyl-3-methyl-pyridin-2-yl)-2,2-dimethyl-propionamide (17.6 g, 69%) as an off-white crystalline solid. mp 72-75° C.; Rf 0.43 (50% ethyl acetate in hexanes); 1H NMR (DMSO-d6, 300 MHz) δ 9.48 (s, 1H), 7.53 (d, J=7.8 Hz, 1 H), 7.48 (d, J=7.5 Hz, 1 H), 2.65 (q, J=7.5 Hz, 2 H), 2.02 (s, 3 H), 1.20 (s, 9 H), 1.18 (t, J=7.5 Hz, 3 H); LRMS calcd for C13H20N2O: 220.3; found 220.0 (M)+. Anal. Calcd for C13H20N2O : C, 70.87; H, 9.15; N, 12.72. Found C, 70.70; H, 9.18; N, 12.74.

후처리

  1. additionAfter the addition
  2. temperaturewarmed to room temperature
  3. extractionextracted with diethyl ether
  4. dry with materialdried over MgSO4
  5. filtrationThe resulting solution is filtered through a short pad of silica gel
  6. concentrationconcentrated
  7. customrecrystallized from heptane

출처 및 근거

ORD 기록
ord-73aea3d4fa2c457dbd6fe1958143f382
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361671B2

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