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

HRID 43177

反応式

HRID 43177 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

SelectFluor (105 mg, 0.30 mmol) was added to a cold (−5° C.) solution of 8-(3,5-dimethoxyphenyl)-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 it 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).

後処理

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

出典と根拠

ORDレコード
ord-f71699c034e54a78943686a89c9b4ade
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

関連ノート

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