Sodium Bicarbonate → 8-(2-Fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid ethyl ester

HRID 2409739Notes

Reaction equation

HRID 2409739 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[CH2:22]([O:24][C:25]([C:27]1[C:28]2[N:29]=[CH:30][CH:31]=[N:32][C:33]=2[C:34]([C:37]2[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[C:39]([O:45][CH3:46])[CH:38]=2)=[CH:35][CH:36]=1)=[O:26])[CH3:23].C([O-])(O)=O.[Na+]>CC#N.CCOC(C)=O>[CH2:22]([O:24][C:25]([C:27]1[C:28]2[N:29]=[CH:30][CH:31]=[N:32][C:33]=2[C:34]([C:37]2[CH:38]=[C:39]([O:45][CH3:46])[CH:40]=[C:41]([O:43][CH3:44])[C:42]=2[F:21])=[CH:35][CH:36]=1)=[O:26])[CH3:23]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724933SelectfluorHCID 669146908-(3,5-Dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester

Product 1

HCID 669147948-(2-Fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid ethyl esterYield 46.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

SelectFluor (105 mg, 0.30 mmol) was added to a cold (−5° C.) solution of 8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 115.1) (100 mg, 0.30 mmol) in CH3CN (2 mL), under an argon atmosphere. The reaction mixture was allowed to warm to rt over 6 h and stirred at that temperature for additional 12 h and diluted in EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 50 mg of the title compound as an off-white solid. Title compound: ESI-MS: 357.2 [M+H]+; tR=4.58 min (System 1); TLC: Rf=0.24 (Hex/EtOAc, 3:2).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Sources & evidence

ORD record
ord-614950ccca9747a68808cdbc80f0c431
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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