(Diethylamino)sulfur trifluoride → 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-8-fluoro-1,2,4-triazolo[4,3-alpha]pyridin-3(2H)-one

HRID 1967

반응식

HRID 1967 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:22](=[O:23])[N:16]2[CH2:17][CH2:18][CH2:19][CH:20](O)[C:15]2=[N:14]1.C(N(S(F)(F)[F:30])CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:22](=[O:23])[N:16]2[CH2:17][CH2:18][CH2:19][CH:20]([F:30])[C:15]2=[N:14]1

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 883229865,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-8-hydroxy-1,2,4-triazolo[4,3-alpha]pyridin-3(2H)-one

생성물 1

HCID 883232485,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-8-fluoro-1,2,4-triazolo[4,3-alpha]pyridin-3(2H)-one수율 90.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 300 mg (0.847 mmol) of 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-8-hydroxy-1,2,4-triazolo[4,3-α]pyridin-3(2H)-one in 10 mL of dichloromethane was added 123 mL (0.930 mmol) of diethylaminosulfur trifluoride (DAST) at -78° C. The reaction mixture was stirred at -78° C. for 4h. The mixture was warmed to room temperature, quenched with ice, and extracted with dichloromethane. The organic layers were dried (MgSO4), and concentrated under reduced pressure. The crude product was flash chromatographed over silica gel, eluting with a 98:2 v:v mixture of dichloromethane and methanol to give 272 mg of the title product of Step 4 as a yellow solid. 19F NMR (CDCl3, 300 MHz) δ-172; 1H NMR (CDCl3, 300 MHz) δ 7.55 (s,1H), 7.2 (s,1H), 5.6, 5.5 (2m, J=70 Hz,1H), 4.8 (s,2H), 4.0 (m,1H), 3.55 (m,1H), 2.6 (m,1H), 2.5-1.8 (m,4H).

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. customquenched with ice
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed over silica gel
  7. washeluting with a 98:2 v
  8. additionv mixture of dichloromethane and methanol

출처 및 근거

ORD 기록
ord-04601f04a9e04e4b899149b8d86a04b2
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728651

연결된 노트

불러오는 중…