Iodine → HCID 178477877, compound

HRID 2211939Notes

Reaction equation

HRID 2211939 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[I:11]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 807IodineHCID 4175246-chloro-1H-indazole

Product 1

HCID 178477877HCID 178477877, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-chloroindazole (1-3, 5.24 g, 34.3 mmol) in ethanol (500 mL) was reacted at the ambient temperature with iodine (8.72 g, 34.3 mmol) in the presence of silver sulfate (10.7 g, 34.3 mmol). After 2 h stirring at the same temperature, all the precipitates were removed by filtration and the filtrate solution was concentrated in vacuo. Trituation with dichloromethane and hexanes gave the desired product as an orange solid (1-4); 1H NMR (400 MHz, DMSO-d6) δ 13.62 (bs, 1H), 7.66 (d, 1H, J=1.6 Hz), 7.46 (d, 1H, J=8.5 Hz), 7.21 (dd, 1H, J=8.6, 1.6 Hz).

Workup

  1. customall the precipitates were removed by filtration
  2. concentrationthe filtrate solution was concentrated in vacuo

Sources & evidence

ORD record
ord-57e59bd162334687aa25711d0bae0346
Source dataset
uspto-grants-2006_09
Patent number
US07101884B2

Reaction notes

Loading…