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

HRID 64174

Reaction equation

HRID 64174 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 178477754HCID 178477754, compoundCatalyst

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3beae237025b4131ad50a76acee9cc57
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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