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

HRID 1908739ノート

反応式

HRID 1908739 の反応式
[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

参加物

4

反応物 1

HCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5cdf930e6d7143888052d2fe457f9de3
出典データセット
uspto-grants-2013_12
特許番号
US08598208B2

反応ノート

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