Nitrogen → N-(3-(6-methoxypyridin-3-yl)-5-nitrophenyl)acetamide

HRID 64142

반응식

HRID 64142 반응식
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.N#N.[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22]([C:2]2[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

생성물 1

HCID 117777422N-(3-(6-methoxypyridin-3-yl)-5-nitrophenyl)acetamide수율 81%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of N-(3-bromo-5-nitrophenyl)acetamide (1 g, 3.86 mmol) in 1,2-dimethoxyethane (20 ml) was degassed by N2 bubbling for 5 min. (6-Methoxypyridin-3-yl)boronic acid (0.77 g, 5.0 mmol, 1.3 eq.) was added and the mixture was degassed for 5 min. Pd(dppf)Cl2 (0.630 g, 0.77 mmol, 0.2 eq.) and aqueous sodium carbonate (1.23 g, 11.58 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane) to give the product in 81% yield (0.9 g).

후처리

  1. additionwas added
  2. customthe mixture was degassed for 5 min
  3. customThe crude residue of the product was purified by column chromatography (60-120 silica gel, 40% ethyl acetate in hexane)
  4. customto give the product in 81% yield (0.9 g)

출처 및 근거

ORD 기록
ord-fb6aa7ef1ade44179475dea6b4cadbe6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

연결된 노트

불러오는 중…