Pyridine → n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide

HRID 12156

反応式

HRID 12156 の反応式
[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:6]([C:5]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[C:4]=2[N+:16]([O-:18])=[O:17])=[O:8])=[N:27][CH:28]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 706222-Amino-5-bromopyridineHCID 971163,4,5-Trimethoxy-2-nitrobenzoic acid

生成物 1

HCID 22596319n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3,4,5-trimethoxy-2-nitrobenzoic acid (0.5 g, 1.95 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.34 ml, 3.9 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-bromopyridine (0.81 g, 4.7 mmol) and pyridine (0.94 ml, 11.7 mmol) were added to the solution. The mixture was stirred at r.t. overnight. After the evaporation of the solvent, the crude residue was purified by silica gel column chromatography using solvent system 25% ethyl acetate in hexane as eluent to give N-(5-bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide as a solid (790 mg; 98%). MS found for C15H14BrN3O6 M+=412, (M+2)+=414.

後処理

  1. customAfter the evaporation of the solvent
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred at r.t. overnight
  4. customAfter the evaporation of the solvent
  5. customthe crude residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a210a4371d564766a8f0071baf727a04
出典データセット
uspto-grants-2010_06
特許番号
US07727981B2

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