Tert-butyl 3-tert-butoxycarbonylamino-6-ethoxy-7-fluoro-5-nitroindazole-1-carboxylate → Tert-butyl 5-amino-3-tert-butoxycarbonylamino-6-ethoxy-7-fluoroindazole-1-carboxylate

HRID 222382Notes

Reaction equation

HRID 222382 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:17]2[C:12](=[C:13]([F:24])[C:14]([O:21][CH2:22][CH3:23])=[C:15]([N+:18]([O-])=O)[CH:16]=2)[N:11]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Ni]>[NH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([F:24])[C:14]=1[O:21][CH2:22][CH3:23])[N:11]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[N:10]=[C:9]2[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

Participants

5

Reactant 2

HCID 68921808Tert-butyl 3-tert-butoxycarbonylamino-6-ethoxy-7-fluoro-5-nitroindazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57908840Tert-butyl 5-amino-3-tert-butoxycarbonylamino-6-ethoxy-7-fluoroindazole-1-carboxylateYield 36%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4.2 2.50 g of tert-butyl 3-tert-butoxycarbonylamino-6-ethoxy-7-fluoro-5-nitroindazole-1-carboxylate are hydrogenated in 20 ml of methanol at RT (catalyst: Raney nickel 0.5 g, hydrogen uptake: 300 ml). The reaction batch is filtered and evaporated. Purification of the residue by column chromatography on silica gel (eluent: petroleum ether: ethyl acetate 7:3) gives 3.30 g (36%) of tert-butyl 5-amino-3-tert-butoxycarbonylamino-6-ethoxy-7-fluoroindazole-1-carboxylate, MS-FAB (M+H+)=441.

Workup

  1. filtrationThe reaction batch is filtered
  2. customevaporated
  3. customPurification of the residue by column chromatography on silica gel (eluent: petroleum ether: ethyl acetate 7:3)

Sources & evidence

ORD record
ord-0e554514373a4c33948e8fece97d9aa8
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

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