Nitrogen → N-(2',6'-difluoro-5-nitrobiphenyl-3-yl)acetamide

HRID 64136

反応式

HRID 64136 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.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1B(O)O.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]>[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1

参加物

7

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343362,6-Difluorophenylboronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

生成物 1

HCID 117777574N-(2',6'-difluoro-5-nitrobiphenyl-3-yl)acetamide収率 94%

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) (20 g, 77 mmol) in 1,2-dimethoxyethane (250 ml) was degassed by N2 bubbling for 5 min. 2,6-Difluorophenylboronic acid (14.6 g, 92.4 mmol, 1.2 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (6.28 g, 7.7 mmol, 0.1 eq.) and aqueous sodium carbonate (24.49 g, 231 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, 30% ethyl acetate in hexane) to give the product in 94% yield (21.2 g). LC-MS (ESI): Calculated mass: 292.24; Observed mass: 293.1 [M+H]+ (rt: 1.49 min).

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, 30% ethyl acetate in hexane)
  3. customto give the product in 94% yield (21.2 g)
  4. custom293.1 [M+H]+ (rt: 1.49 min)

出典と根拠

ORDレコード
ord-0ae67e8e08ca44d498ab0dcc2f7cbd43
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

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