HCID 69360103, compound → HCID 45095359, compound

HRID 852596Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([N+:16]([O-])=O)[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[N:4]1)[CH3:2]>CO.O.[Pd]>[NH2:16][C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[C:11]2[C:6]=1[CH:5]=[N:4][N:3]2[CH2:1][CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 1-ethyl-4-nitro-1H-indazole-6-carboxylate (D198) (2.2 g, 8.8 mmol, 1 equiv) in MeOH (100 ml) and H2O (10 ml) was added 10% palladium on charcoal (50% wet, 700 mg, 16% w/w) and the resulting mixture was stirred at 60° C. for 30 min then cooled to room temperature. The catalyst was removed by filtration through a pad of celite and most of the solvent removed in vacuo. The residue was partitioned between AcOEt and a saturated aqueous NaHCO3 solution and the two layers were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was triturated with iso-hexane to give methyl 4-amino-1-ethyl-1H-indazole-6-carboxylate (D199) (1.55 g, 80%) which was used in the next step without further purification. [M+H]+=220.1, RT=3.31 min.

Workup

temperaturethen cooled to room temperature
customThe catalyst was removed by filtration through a pad of celite and most of the solvent
customremoved in vacuo
customThe residue was partitioned between AcOEt
customa saturated aqueous NaHCO3 solution and the two layers were separated
dry with materialThe organic phase was dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was triturated with iso-hexane

Sources & evidence

ORD record: ord-9f166f93506d4b30aeabb22d70a9ffc0
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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