Hydrochloric Acid → 5-Fluoro-2-(1-isobutyl-1H-indazol-5-yloxy)-benzylamine

HRID 2112215Notes

Reaction equation

HRID 2112215 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[N:15]=[CH:14]3)=[C:6]([CH:9]=1)[C:7]#[N:8].N#N.Cl>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[N:15]=[CH:14]3)=[C:6]([CH:9]=1)[CH2:7][NH2:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 574187715-Fluoro-2-(1-isobutyl-1H-indazol-5-yloxy)-benzonitrile

Product 1

HCID 574841225-Fluoro-2-(1-isobutyl-1H-indazol-5-yloxy)-benzylamineYield 107.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-fluoro-2-(1-isobutyl-1H-indazol-5-yloxy)-benzonitrile (3.05 g, 9.86 mmol) purged with N2 in MeOH (50 mL) was added concentrated HCl (1.6 mL) and Pd(OH)2/C (15% wt, 0.457 g). The mixture was stirred at room temperature for 18 hours under H2 atmosphere. The catalyst was removed by filtration and the solution was concentrated under reduced pressure to afford 3.32 g of pale yellow foam (96% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f9b1571ec3054ba39e3c6a1a0cfd7e5e
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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