Water → 2-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester

HRID 245079ノート

反応式

HRID 245079 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.[Br-].[CH3:15][CH2:16][CH:17]([Zn+])[CH2:18][CH3:19].O>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:17]([CH2:18][CH3:19])[CH2:16][CH3:15])[CH:5]=1

参加物

5

反応物 3

HCID 962WaterHCID 13339618Methyl 2-chloro-6-methoxyisonicotinateHCID 178456109HCID 178456109、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
85 °C

実験手順

Under argon, Pd(dppf) (3.04 g, 4 mmol) is added to a solution of 2-chloro-6-methoxy-isonicotinic acid methyl ester (50 g, 0.248 mol) in THF (100 mL). A 0.5 M solution of 3-pentylzincbromide in THF (550 mL) is added via dropping funnel. Upon complete addition, the mixture is heated to 85° C. for 18 h before it is cooled to rt. Water (5 mL) is added and the mixture is concentrated. The crude product is purified by filtration over silica gel (350 g) using heptane:EA 7:3 to give 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid methyl ester (53 g) as a pale yellow oil; 1H NMR (CDCl3): δ0.79 (t, J=7.5 Hz, 6H), 1.63-1.81 (m, 4H), 2.47-2.56 (m, 1H), 3.94 (s, 3H), 3.96 (s, 3H), 7.12 (d, J=1.0 Hz, 1H), 7.23 (d, J=1.0 Hz, 1H).

後処理

  1. additionUpon complete addition
  2. temperatureis cooled to rt
  3. concentrationthe mixture is concentrated
  4. filtrationThe crude product is purified by filtration over silica gel (350 g)

出典と根拠

ORDレコード
ord-6afaebd5f60645648aa23aa8fecedf76
出典データセット
uspto-grants-2014_02
特許番号
US08658675B2

反応ノート

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