Dichloromethane → 6-fluoro-1H-indazol-5-amine

HRID 227717Notes

Reaction equation

HRID 227717 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[N+:11]([O-])=O.C(Cl)Cl.[H][H]>[Pd].CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH2:11]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 459336676-Fluoro-5-nitro-1H-indazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 450905046-fluoro-1H-indazol-5-amineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the product of Step (c) (530 mg, 2.93 mmol, 1 equiv) and 10% Pd/C (200 mg) was added CH2Cl2 (10 mL) and MeOH (40 mL). The atmosphere was replaced with hydrogen gas and the solution was stirred at room temperature and atmospheric pressure for 2 hours. The reaction mixture was filtered through a plug of celite and rinsed with MeOH and CH2Cl2. The residue was purified by flash chromatography (linear gradient, 40→70% EtOAc/hexanes) affording 330 mg (75%) of the title compound as a pale purple solid. MS (ES+) m/e 152 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washrinsed with MeOH and CH2Cl2
  3. customThe residue was purified by flash chromatography (linear gradient, 40→70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-615325a38229463e82c38a74f1860b59
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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