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

HRID 64136

Reaction equation

HRID 64136 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.[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

Participants

7

Reactant 4

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

Product 1

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

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) (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).

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, 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)

Sources & evidence

ORD record
ord-0ae67e8e08ca44d498ab0dcc2f7cbd43
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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