Potassium Carbonate → 7-(4-Fluoro-3-nitrophenyl)-2-(morpholin-4-yl)quinoxalin

HRID 524372Notes

Reaction equation

HRID 524372 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][C:26]=1[N+:34]([O-:36])=[O:35]>C1COCC1.O>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:11]=[C:10]3[C:5]([N:6]=[CH:7][C:8]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)=[N:9]3)=[CH:4][CH:3]=2)=[CH:27][C:26]=1[N+:34]([O-:36])=[O:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 249017654-Fluoro-3-nitrophenylboronic acidHCID 533635264-(7-Bromoquinoxalin-2-yl)morpholine

Product 1

HCID 670349977-(4-Fluoro-3-nitrophenyl)-2-(morpholin-4-yl)quinoxalinYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-bromo-2-morpholin-4-yl-quinoxaline (1 g, 3.4 mmol), potassium carbonate (0.56 g, 4.1 mmol) and [1,1,-Bis(diphenlyphosphino)ferrocene]palladium(II)chloride (0.83 g, 1.0 mmol) in THF (38 mL) and water (3.8 mL) was added (4-fluoro-3-nitrophenyl)boronic acid (1.26 g, 6.8 mmol). The reaction mixture was allowed to reflux for 6 h. After cooling to room temperature, the solvent was removed and the residue was purified by chromatography (silica gel, Hexane/EtOAc: 20%->100% EtOAc) giving rise to 1.1 g (92%) of the desired product.

Workup

  1. temperatureto reflux for 6 h
  2. customthe solvent was removed
  3. customthe residue was purified by chromatography (silica gel, Hexane/EtOAc: 20%->100% EtOAc)

Sources & evidence

ORD record
ord-8c0181296ba3465ebd822e1ce588b7cf
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

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