Ammonium Chloride → 3-bromo-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine

HRID 1790172Notes

Reaction equation

HRID 1790172 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][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][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[N:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 220366263-bromo-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Product 1

HCID 696526623-bromo-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamineYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-bromo-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (0.90 g, 2.7 mmol), iron powder (1.5 g, 26 mmol), and ammonium chloride (73 mg, 1.3 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 about 15 minutes, filtered through a plug of silica gel, which was rinsed with triethylamine/ethyl acetate (1/4), and the filtrate concentrated under reduce pressure to provide the title compound (0.78 g, 95%). 1H NMR (300 MHz, DMSO-d6) ppm 1.64 (m, 4H), 2.46 (m, 4H), 2.79 (t, 2H, J=6.44), 4.23 (t, J=6.44, 2H), 5.56 (s, 2H), 6.49 (m, 1H), 6.58 (m, 1H), 7.16 (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

Sources & evidence

ORD record
ord-82339a0c5f9a4a9eb8ee8a1ec45299e4
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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