Stannous Chloride → HCID 53244426, compound

HRID 407155Notes

Reaction equation

HRID 407155 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:15][N:16]3C(OC(C)(C)C)=O)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:15][NH:16]3)=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 68620615HCID 68620615, compound

Product 1

HCID 53244426HCID 53244426, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-tert-butyl 3-ethyl 6-(4-nitrophenyl)-1H-indazole-1,3-dicarboxylate (879 mg, 2.14 mmol) in ethanol (40 Ml), was added SnCl2 (2.4 g, 10.7 mmol) and the mixture was stirred at 80° C. for 3 h. The mixture was cooled to room temperature and saturated sodium bicarbonate aqueous solution was added. The organic layer was extracted three times and the combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was triturated in ethyl acetate and hexane to give ethyl 6-(4-aminophenyl)-1H-indazole-3-carboxylate (442 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe organic layer was extracted three times
  3. dry with materialthe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-dbf4c93a61cd4658be32b126ebd89af7
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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