Methanol → 5-Methyl-1H-indazol-4-amine

HRID 1443220Notes

Reaction equation

HRID 1443220 reaction equation
Cl[C:2]1[C:3]([NH2:11])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH3:12]O>[Pd]>[CH3:12][C:2]1[C:3]([NH2:11])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 887MethanolHCID 179892615-Chloro-1H-indazol-4-amine

Product 1

HCID 193544325-Methyl-1H-indazol-4-amineYield 6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Analogously to the production of 5-chloro-1H-indazol-4-ylamine, the regioisomeric mixture of the previous reaction (1.0 g, 5.64 mmol)) is reacted with 100 mg of palladium on carbon in methanol under hydrogen atmosphere for 16 hours at room temperature. After purification on silica gel with hexane/ethyl acetate (33% hexane, then 100% ethyl acetate), 53 mg (6% of theory) of 5-methyl-1H-indazol-4-ylamine is obtained.

Workup

  1. customAfter purification on silica gel with hexane/ethyl acetate (33% hexane

Sources & evidence

ORD record
ord-bbca41883f3043539429aa866db67940
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

Loading…