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

HRID 64142

反応式

HRID 64142 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fb6aa7ef1ade44179475dea6b4cadbe6
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

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