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

HRID 2195535

반응식

HRID 2195535 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].[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

참가 물질

5

반응물 3

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

생성물 1

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

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 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-2eece15bb868492e885db24154f98c9c
출처 데이터셋
uspto-grants-2012_12
특허 번호
USRE043878E1

연결된 노트

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