Methyl 2-chloro-6-methoxyisonicotinate → 2-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester

HRID 1908739노트

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HRID 1908739 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6](Cl)[CH:5]=1>O1CCOCC1.C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH:4]([CH2:9][CH3:8])[CH2:5][CH3:6])[CH:5]=1

참가 물질

4

반응물 1

HCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

생성물 1

HCID 670268752-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester수율 99.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

Under argon, Pd(dppf) (83 mg, 101 μmol) is added to a solution of 2-chloro-6-methoxy-isonicotinic acid methyl ester (2.00 g, 9.92 mmol, see preparation of 2-isobutyl-6-methoxy-isonicotinic acid) in dioxane (30 mL). To this mixture, a solution of 1-ethyl-propyl zinkbromide (1.17 g, 9.92 mmol, 20 mL of a 0.5 M solution in THF) is added. The mixture is stirred at 85° C. for 16 h before the reaction is carefully quenched with water and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid methyl ester (1.17 g) as a pale yellow oil; LC-MS: tR=1.08 min; [M+1]+=238.03.

후처리

  1. customis carefully quenched with water
  2. extractionextracted twice with EA
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

출처 및 근거

ORD 기록
ord-5cdf930e6d7143888052d2fe457f9de3
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598208B2

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