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

HRID 514721

반응식

HRID 514721 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 22596319n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide수율 98.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dab9550dd4164c2db31d42a0d8c82895
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108922B2

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