Hydrochloric Acid → HCID 178434281, compound

HRID 706643Notes

Reaction equation

HRID 706643 reaction equation
C[Zn]C.I[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N+:14]([O-:16])=[O:15])[NH:7][N:6]=1.[CH3:17]O.Cl>O1CCOCC1.C(Cl)Cl>[CH3:17][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N+:14]([O-:16])=[O:15])[NH:7][N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178477796HCID 178477796, compoundHCID 178526562HCID 178526562, compound

Product 1

HCID 178434281HCID 178434281, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of dimethyl zinc (1.73 ml, 3.46 mmol) was added dropwise to a mixture of 3-iodo-4-nitro-1H-indazole (0.500 g, 1.73 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (0.427 g, 0.519 mmol) in dioxane (0.2M, 9 mL) under argon. The mixture was heated under reflux for 2 hours. After cooling, MeOH (<1 mL) was added, followed by 2N HCl (1 mL) and DCM (5 mL). After stirring mixture for 30 minutes, the organic layer was separated, washed with saturated aqueous sodium bicarbonate, water, and brine. The combined organic extracts were dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (1-10% EtOAc in DCM to provide 3-methyl-4-nitro-1H-indazole (0.082 g, 27% yield) as a brown residue.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. washwashed with saturated aqueous sodium bicarbonate, water, and brine
  6. customThe combined organic extracts were dried
  7. addition(phase separator silicone treated filter paper)
  8. concentrationconcentrated
  9. custompurified on silica gel (1-10% EtOAc in DCM

Sources & evidence

ORD record
ord-0262a10af41748848a737eaee678e86c
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…