Nitrogen → N-(4'-methoxy-5-nitrobiphenyl-3-yl)acetamide

HRID 64133

Reaction equation

HRID 64133 reaction equation
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.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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]>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Product 1

HCID 89500151N-(4'-methoxy-5-nitrobiphenyl-3-yl)acetamideYield 73%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (1 g, 3.8 mmol) in 1,2-dimethoxyethane (20 ml) was degassed by N2 bubbling for 5 min. 4-Methoxyphenylboronic acid (0.69 g, 4.4 mmol, 1.1 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.31 g, 0.38 mmol, 0.1 eq.) and aqueous sodium carbonate (1 g, 9.5 mmol, 2.5 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, 40% ethyl acetate in hexane) to give the product in 73% yield (0.8 g).

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, 40% ethyl acetate in hexane)
  3. customto give the product in 73% yield (0.8 g)

Sources & evidence

ORD record
ord-7f521d9771d748b7b36091019320dce1
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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