HCID 23365859, compound → Methyl 4-[6-amino-3-methoxyindazol-1-ylmethyl]-3-methoxybenzoate

HRID 1646360Notes

Reaction equation

HRID 1646360 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[N:5]([CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])[N:4]=1>C(OCC)(=O)C.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:3]([O:2][CH3:1])=[N:4][N:5]2[CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 23365859HCID 23365859, compound

Product 1

HCID 23365880Methyl 4-[6-amino-3-methoxyindazol-1-ylmethyl]-3-methoxybenzoateYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium-on-carbon (5% w/w, 0.24 g.) was added to a solution of indazole (U) (0.48 g.) in ethyl acetate (25 ml.). The mixture was hydrogenated at 1.1 bars for 3 hours. The catalyst was removed by filtration through diatomaceous earth, and the filtrate evaporated. The residue was recrystallized from a hot ethyl acetate/petroleum ether mixture to give methyl 4-(6-amino-3-methoxyindazol-1-ylmethyl)-3-methoxybenzoate (S) (0.15 g., 34%), as a pale-yellow solid, m.p. 188°-193° C.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate evaporated
  3. customThe residue was recrystallized from a hot ethyl acetate/petroleum ether mixture

Sources & evidence

ORD record
ord-ac310ededa3449109d13d6b9dcd403f9
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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