Phosphorus oxychloride → 4-Chloro-2-(2,6-dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine

HRID 2366318노트

반응식

HRID 2366318 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[C:10]1[S:11][C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[C:16]([F:19])[C:17]=2[N:18]=1.P(Cl)(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>ClCCCl>[Cl:23][C:13]1[C:12]2[S:11][C:10]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([I:8])=[CH:5][C:4]=3[Cl:9])=[N:18][C:17]=2[C:16]([F:19])=[CH:15][N:14]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 668013882-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine-5-oxide

생성물 1

HCID 866690314-Chloro-2-(2,6-dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine수율 34%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a suspension of 2-(2,6-dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine-5-oxide (2.8 g, 6.4 mmol) in 1,2-dichloroethane (80 mL) was added phosphorus oxychloride (1.8 mL, 19.1 mmol). The reaction mixture was heated under reflux for 16 hours. Upon cooling, the resultant mixture was treated cautiously with aqueous sodium bicarbonate to achieve pH 6-7, and then extracted with dichloromethane (×2). The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 0-50% diethyl ether in petroleum ether to afford the title compound as a white solid (1.0 g, 34% yield). 1H NMR (400 MHz, CDCl3): δ 8.35 (d, J=1.5 Hz, 1H), 7.82 (s, 2H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureUpon cooling
  4. extractionextracted with dichloromethane (×2)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel eluting with 0-50% diethyl ether in petroleum ether

출처 및 근거

ORD 기록
ord-059a07506a8d412f8bfd221b90ce2e05
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697708B2

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