Dimethylformamide → 4-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole

HRID 1790095Notes

Reaction equation

HRID 1790095 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].[C:13](=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][CH:23]1CCNCC1.[CH3:29][N:30]([CH:32]=O)[CH3:31]>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][CH2:29][N:30]1[CH2:32][CH2:23][CH2:22][CH2:21][CH2:31]1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 180574-NitroindazoleHCID 219374464-(2-Chloroethyl)piperidine hydrochloride

Product 1

HCID 220365934-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole

Conditions

Temperature
60 °C

Procedure

4-Nitroindazole (mmol) and potassium carbonate (mmol) in 60 mL of DMF was added was stirred for 30 minutes, after which 4-(2-chloro-ethyl)-piperidine hydrochloride (mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and the mixture filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure, and the residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.39 (m, 6 H), 2.36 (m, 4 H), 2.73 (t, J=6.44 Hz, 2 H), 4.63 (t, J=6.44 Hz, 2 H), 7.64 (m, 1 H), 8.16 (m, 1 H), 8.28 (m; 1 H), 8.51 (s, 1 H); MS (DCI/NH3) m/z 275 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe mixture filtered through a plug of silica gel which
  3. washwas rinsed with triethylamine/ethyl acetate (1/4)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-68a75aedd2c544b48f0ee06471fa621f
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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