Pyridine → Ethyl 1-(4-fluorophenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1662019

反応式

HRID 1662019 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.N1C=CC=CC=1>O1CCOCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:5]2[C:6]([CH3:8])=[CH:7][C:2]([CH3:1])=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]2=[O:9])=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 247443Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylateHCID 2856454-Fluorophenylboronic acid

生成物 1

HCID 66767119Ethyl 1-(4-fluorophenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate収率 16.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A suspension of ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (5.0 g, 0.025 mol), 4-fluorophenylboronic acid (10.7 g, 0.077 mol), cupric acetate (1.33 g, 0.007 mol), pyridine (6.86 mL), and 4 A molecular sieves (5.0 g) in 1,4-dioxane (80 mL) is heated at 80° C. for 68 hours. The solids are filtered off and the filtrate is concentrated. The residue is partitioned with EtOAc (50 mL) and 2N HCl (70 mL). The precipitated solid is collected by filtration and washed with EtOAc to give the title product (1.2 g). The EtOAc filtrate is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc:MeOH (40:20:1) to give another portion of product (0.12 g), (1.32 g total, 17.8% yield). MS (m/z): 290.1 (M+H).

後処理

  1. filtrationThe solids are filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is partitioned with EtOAc (50 mL) and 2N HCl (70 mL)
  4. filtrationThe precipitated solid is collected by filtration
  5. washwashed with EtOAc

出典と根拠

ORDレコード
ord-6cf3d172ad5f4598a06a58d9bc8a9698
出典データセット
uspto-grants-2011_10
特許番号
US08030302B2

関連ノート

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