Nitrogen → N-(5-nitrobiphenyl-3-yl)acetamide

HRID 64130

反応式

HRID 64130 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.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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]>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1)([O-:10])=[O:9]

参加物

7

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

生成物 1

HCID 89500237N-(5-nitrobiphenyl-3-yl)acetamide収率 61%

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 of Example 1(c) (1 g, 3.87 mmol) in 1,2-dimethoxyethane (20 ml) was degassed by N2 bubbling for 5 min. Phenyl-boronic acid (0.61 g, 5.04 mmol, 1.3 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.63 g, 0.77 mmol, 0.2 eq.) and aqueous sodium carbonate (1.23 g, 11.6 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, 50% ethyl acetate in hexane) to give the product in 61% yield (0.6 g).

後処理

  1. customthe mixture was degassed for another 5 min
  2. customThe crude residue of the product was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane)
  3. customto give the product in 61% yield (0.6 g)

出典と根拠

ORDレコード
ord-d7937579df9c41098c17dc381f3d5ca0
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

関連ノート

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