Ammonium Chloride → HCID 69652705, compound

HRID 1790167Notes

Reaction equation

HRID 1790167 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22036566HCID 22036566, compound

Product 1

HCID 69652705HCID 69652705, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (1.9 g, 5.6 mmol), iron powder (3.1 g, 56 mmol), and ammonium chloride (0.15 g, 2.8 mmol) in 80% ethanol was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and stirred in triethylamine/ethyl acetate (1/4, 20 mL) for 15 minutes, filtered through a plug of silica gel, which was rinsed with triethylamine/ethyl acetate (1/4), and the filtrate concentrated under reduced pressure to provide the title compound (1.2 g, 70%). 1H NMR (300 MHz, DMSO-d6) ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.81 (t, 2H, J=6.44), 4.36 (t, J=6.44, 2H), 5.05 (s, 2H), 6.52 (m, 1H), 6.88 (m, 1H), 7.42 (m, 1H); MS (DCI/NH3) m/z 309 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica gel, which
  5. washwas rinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce051226ad6b4516a6a667311b4efcc1
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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