Nitrogen → N-(3-(3-fluoropyridin-2-yl)-5-nitrophenyl)acetamide

HRID 64174

反応式

HRID 64174 の反応式
[N+:1]([C:4]1[CH:5]=[C:6](CC(N)=O)[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)([O-:3])=[O:2].[N:23]#N.Cl[C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C[O:40][CH2:41][CH2:42]OC>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[F:32][C:31]1[C:26]([C:8]2[CH:7]=[C:6]([NH:23][C:41](=[O:40])[CH3:42])[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=2)=[N:27][CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 5

HCID 947NitrogenHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27827912-Chloro-3-fluoropyridineHCID 1317372153-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-acetamide

生成物 1

HCID 89500321N-(3-(3-fluoropyridin-2-yl)-5-nitrophenyl)acetamide収率 70%

試薬・触媒・溶媒 1

HCID 178477754HCID 178477754、化合物触媒

実験手順

A solution of N-(3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-acetamide (10 g, 32.67 mmol) in 1,2-dimethoxyethane (100 ml) was degassed by N2 bubbling for 5 min. 2-Chloro-3-fluoro pyridine (4.29 g, 32.67 mmol) was added and the mixture was degassed for another 5 min. Pd(dppf)cl2 (2.6 g, 3.26 mmol) and aqueous sodium carbonate (10.39 g, 98.03 mmol) 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, 3% methanol in chloroform) to yield the title product in 70% yield (6.3 g). 1H NMR (300 MHz, DMSO-d6): δ10.64 (s, 1H), 8.74 (m, 1H), 8.62 (m, 1H), 8.55, (brs, 1H), 8.44 (brs, 1H), 7.93 (m, 1H), 7.60 (m, 1H), 2.12 (s, 3H).

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, 3% methanol in chloroform)

出典と根拠

ORDレコード
ord-3beae237025b4131ad50a76acee9cc57
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

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