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

HRID 64174

반응식

HRID 64174 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 178477754HCID 178477754, 화합물촉매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3beae237025b4131ad50a76acee9cc57
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

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