Phosphorus oxychloride → 4-Chloro-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine

HRID 573567

반응식

HRID 573567 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:16](=O)[CH:15]=[CH:14][NH:13][C:12]=3[S:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[S:11][CH:10]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:17]=12

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 683240213-[3-(Methyloxy)phenyl]thieno[2,3-b]pyridin-4(7H)-one

생성물 1

HCID 683237304-Chloro-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine수율 85.1%

반응 조건

온도
110 °C

실험 절차

A mixture of 3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4(7H)-one (Description 42) (465 mg, 1.807 mmol) and phosphorus oxychloride (5 mL, 53.6 mmol) was heated at 110° C. for 1 h. After cooling to RT, the mixture was poured onto ice, stirred for 30 min and then extracted with DCM (10 mL×3). The organic layers were combined, washed with saturated NaHCO3 solution (100 mL), brine (100 mL), filtered through phase separator and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-40% ethyl acetate in cyclohexane, to give the title compound (424 mg). LCMS (A) m/z: 278 [M+1]+, Rt 1.33 min (acidic).

후처리

  1. temperatureAfter cooling to RT
  2. additionthe mixture was poured onto ice
  3. extractionextracted with DCM (10 mL×3)
  4. washwashed with saturated NaHCO3 solution (100 mL), brine (100 mL)
  5. filtrationfiltered through phase separator
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a gradient of 0-40% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-064ceb6aef93410ba0815f911a6328a6
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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