Potassium Fluoride → N-(5-((5-bromo-3-nitropyridin-2-yl)amino)-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide

HRID 64150

반응식

HRID 64150 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])[CH:7]=1.[Br:20][C:21]1[CH:22]=[C:23]([N+:28]([O-:30])=[O:29])[C:24](Cl)=[N:25][CH:26]=1.[F-].[K+]>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]([N+:28]([O-:30])=[O:29])[C:24]([NH:1][C:2]2[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([C:8]3[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=3[F:15])[CH:7]=2)=[N:25][CH:26]=1

참가 물질

5

반응물 3

HCID 522689Potassium FluorideHCID 70194125-Bromo-2-chloro-3-nitropyridineHCID 89500157N-(5-amino-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide

생성물 1

HCID 117777719N-(5-((5-bromo-3-nitropyridin-2-yl)amino)-2',6'-difluoro-[1,1'-biphenyl]-3-yl)acetamide수율 28%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-(5-amino-2′,6′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (1.4 g, 6.1 mmol), 5-bromo-2-chloro-3-nitropyridine (1.6 g, 6.1 mmol, 1.0 eq.) and potassium fluoride (0.53 g, 9.0 mmol, 1.5 eq.) in DMF (8 ml) was heated at 110° C. for 4 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude product which was purified by column chromatography (60-120 silica gel, 30% Ethyl acetate in hexane) to give the title product in 28% yield (0.8 g).

후처리

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the crude product which
  5. customwas purified by column chromatography (60-120 silica gel, 30% Ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-617f241a9e4c4fe1aee17f66a38e319f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

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