Selectfluor → HCID 59292824、化合物

HRID 1189898ノート

反応式

HRID 1189898 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[CH:28]=[CH:29][C:30]([C:37]2[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[C:39]([O:45][CH3:46])[CH:38]=2)=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:26])[CH3:23]>CC#N>[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[CH:29][C:30]([C:37]2[CH:38]=[C:39]([O:45][CH3:46])[CH:40]=[C:41]([O:43][CH3:44])[C:42]=2[F:21])=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:26])[CH3:23]

参加物

4

反応物 2

HCID 2724933SelectfluorHCID 592928505-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

生成物 1

HCID 59292824HCID 59292824、化合物収率 34.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

SelectFluor (2.04 g, 5.8 mmol, 2 equiv) was added to a cold (−5° C.) solution of 5-(3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 174.2) (970 mg, 2.9 mmol) in CH3CN (40 mL), under an argon atmosphere. The reaction mixture was allowed to warm to rt, stirred at that temperature for 6 h, quenched by addition of a saturated aqueous solution of NaHCO3, and concentrated. The residue was 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) followed by trituration in Et2O to provide 355 mg of the title compound: ESI-MS: 356.2 [M+H]+; tR=3.80 min (System 1); TLC: Rf=0.18 (Hex/EtOAc, 3:2).

後処理

  1. customquenched by addition of a saturated aqueous solution of NaHCO3
  2. concentrationconcentrated
  3. additionThe residue was diluted in EtOAc
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

出典と根拠

ORDレコード
ord-a9c2e2a7e9824678be07333a1fc5c2e2
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

反応ノート

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