Allyl iodide → 6-Allyloxy-1H-indazole

HRID 2121855

Reaction equation

HRID 2121855 reaction equation
[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]

Participants

6

Reactant 3

HCID 11166Allyl iodide2×HCID 11430Potassium Carbonate2×HCID 1354839876-hydroxy-1H-indazole

Product 1

HCID 224965696-Allyloxy-1H-indazoleYield 56.3%

Reagents, catalysts & solvents 2

HCID 10796Cesium carbonateCatalystHCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7e1a1c176fa04428bd9bfa6d8e1ef594
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Linked notes

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