HCID 68836725, compound → HCID 68833576, compound

HRID 490558Notes

Reaction equation

HRID 490558 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=3)[C:9](=[O:19])[NH:8]2)=[CH:4][CH:3]=1>CO.[Pd]>[NH2:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:5]1[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=1)[NH:8][C:9]2=[O:19]

Participants

4

Reactant 1

HCID 68836725HCID 68836725, compound

Product 1

HCID 68833576HCID 68833576, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(4-fluoro-benzyl)-5-nitro-1,2-dihydro-indazol-3-one (0.81 g) in MeOH (100 mL) was added Pd/C(10%) catalyst (0.1 g) and the reaction mixture was stirred for three hours at 40° C. under a hydrogen atmosphere using a balloon. After this time the reaction mixture was filtered through Celite® which was washed with more EtOAc. The combined organic solution was evaporated in vacuo for afford the desired 5-amino-1-(4-fluoro-benzyl)-1,2-dihydro-indazol-3-one (0.617 g) which was taken into the next reaction without further purification. MS (ESI+): 258.3 ([M+H]+).

Workup

  1. filtrationAfter this time the reaction mixture was filtered through Celite® which
  2. washwas washed with more EtOAc
  3. customThe combined organic solution was evaporated in vacuo

Sources & evidence

ORD record
ord-70a7dcb19b434dfd883f77a9cd7f7fee
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

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