Selectfluor → HCID 59292824, 화합물

HRID 1189898노트

반응식

HRID 1189898 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 59292824HCID 59292824, 화합물수율 34.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a9c2e2a7e9824678be07333a1fc5c2e2
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

반응 노트

불러오는 중…