Pyridine → Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate

HRID 870802ノート

反応式

HRID 870802 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[NH:7][CH:6]=1)=[O:4].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1)=[O:4]

参加物

6

反応物 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 416343Methyl 6-oxo-1,6-dihydropyridine-3-carboxylate

生成物 1

HCID 11989075Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate収率 56%

試薬・触媒・溶媒 2

HCID 165397Cupric acetate monohydrate触媒HCID 6344Dichloromethane溶媒

実験手順

Methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6.0 g, 39.22 mmol), phenylboronic acid (5.74 g, 47.06 mmol), copper(II) acetate monohydrate (11.76 g, 58.82 mmol), pyridine (6.32 mL, 78.43 mmol) and molecular sieves (4 Å, 6.0 g) in dichloromethane (100 mL) was stirred at ambient temperature for 12 hours and filtered. Standard extractive work up provided a crude residue which was purified by silica gel column chromatography (100-200 mesh) (1-2% methanol in chloroform) to give the title compound as a brown solid (5.0 g, 56%). m.p. 100-105° C.; 1H NMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 6.63 (d, J=9.5 Hz, 1H), 7.36-7.55 (m, 5H), 7.91 (dd, J=2.5, 9.9 Hz, 1H), 8.23 (d, J=2.5 Hz, 1H); IR (KBr) ν 3058, 2924, 2854, 1721, 1675, 1540, 1446, 1313, 1271, 1103 cm−1; MS 230 (M+1).

後処理

  1. filtrationfiltered
  2. customStandard extractive work up provided a crude residue which
  3. customwas purified by silica gel column chromatography (100-200 mesh) (1-2% methanol in chloroform)

出典と根拠

ORDレコード
ord-e6aa1c34fc614d28ace763b07c2b902a
出典データセット
uspto-grants-2015_03
特許番号
US08969575B2

反応ノート

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