Pyridine → Ethyl 4,6-dimethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate

HRID 1662020

반응식

HRID 1662020 반응식
[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].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4](=[O:9])[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 247443Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

생성물 1

HCID 13837925Ethyl 4,6-dimethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate수율 31.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A suspension of ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (7.5 g, 0.038 mol), phenylboronic acid (14.1 g, 0.115 mol), cupric acetate (1.38 g, 0.008 mol), pyridine (7.5 mL) in 1,4-dioxane (80 mL) is heated at 80° C. for 96 hours. The solid is filtered off and the filtrate is concentrated. The residue is partitioned with EtOAc (50 mL) and 2N HCl (70 mL), and the precipitate is collected by filtration and washed with EtOAc to give the title product (2.95 g). The EtOAc solution is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with PE:acetone (2:1) to give another portion of (0.3 g). (3.25 g, 31.2% yield). MS (m/z): 272.0 (M+H).

후처리

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

출처 및 근거

ORD 기록
ord-57e49fb0763f41c6a6b13c00bfa96d11
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030302B2

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