Allyl iodide → 6-Allyloxy-1H-indazole

HRID 1815936

반응식

HRID 1815936 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH:18]=[CH2:19]>CC(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH2:19]([O:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][NH:1]2)=[CH:5][CH:6]=1)[CH:18]=[CH2:17]

참가 물질

6

반응물 3

HCID 11166Allyl iodide2회HCID 11430Potassium Carbonate2회HCID 1354839876-hydroxy-1H-indazole

생성물 1

HCID 224965696-Allyloxy-1H-indazole수율 56.3%

시약·촉매·용매 2

HCID 10796Cesium carbonate촉매HCID 180Acetone용매

실험 절차

To a solution of 1H-indazol-6-ol (20.0 g, 150 mmol) in acetone (450 mL) was added pulverized potassium carbonate (22.4 g, 162 mmol), cesium carbonate (2.00 g, 5.7 mmol), and allyl iodide (14.63 mL, 160 mmol) and the mixture was stirred for 18 h at ambient temperature. Additional potassium carbonate (5.00 g, 36 mmol) and allyl iodide (1.4 mL, 15 mmol) were added and the mixture was stirred for 2 h followed filtration. Water (200 mL) was added to the filtrate and the volume of the mixture was reduced by about half in vacuo and extracted with dichloromethane (2×100 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica, 20% to 50% EtOAc/hexane) to give a yellow solid (14.7 g, 56%): mp 110-112° C.; LC/MS (+APCI) m/z 175 (M+H). Unreacted starting material was recovered (4.71 g).

후처리

  1. stirringthe mixture was stirred for 2 h
  2. filtrationfiltration
  3. additionWater (200 mL) was added to the filtrate
  4. extractionextracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated to a residue which
  7. customwas purified by chromatography (silica, 20% to 50% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-dd6fe07f1e8646f1b5c5683ed6a01535
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881749B2

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