Ammonium formate → tert-Butyl 5-amino-3-methyl-1H-indazole-1-carboxylate

HRID 25366

Reaction equation

HRID 25366 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[C:10]([CH3:20])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[N:9]=[C:10]2[CH3:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22567205tert-Butyl 3-methyl-5-nitro-1H-indazole-1-carboxylate

Product 1

HCID 59276571tert-Butyl 5-amino-3-methyl-1H-indazole-1-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Amino-N-tert-butoxycarbonyl-3-methyl-1H-indazole can be obtained as described in Example 6 from 3.4 g of N-tert-butoxycarbonyl-3-methyl-5-nitro-1H-indazole, 50 ml of methanol, 0.61 g of 10% palladium-on-charcoal and 3.53 g of ammonium formate. 2.7 g of 5-amino-N-tert-butoxycarbonyl-3-methyl-1H-indazole are thus obtained in the form of a cream solid melting at 185° C.

Sources & evidence

ORD record
ord-fcdd43b1809b47dfab16fdca94887db9
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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