Potassium Carbonate → 5-Nitro-2-(2-piperidin-1-yl-ethyl)-2H-indazole

HRID 1825829

Reaction equation

HRID 1825829 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C)C=O>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:9]=2)[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

Product 1

HCID 221389205-Nitro-2-(2-piperidin-1-yl-ethyl)-2H-indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-Nitroindazole (1.00 g, 6.13 mmol) and and potassium carbonate (2.50 g, 18.1 mmol) in 20 mL of N,N-dimethylformamide was stirred for 30 minutes and then 1-(2-chloro-ethyl)-piperidine hydrochloride (1.74 g 9.45 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature, filtered through a plug of silica gel and rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under vacuo and the residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30). 1H NMR (300 MHz, DMSO-d6) ppm 1.13–1.15 (m, 6H) 2.40 (m, 4H), 2.82 (t, 2H, J=6.44) 4.61 (t, 2H, J=6.44), 7.78 (m, 1H), 8.00 (m, 1H), 8.81 (s, 1H), 8.90 (d, 1H); MS (DCI/NH3) m/z 275 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a plug of silica gel
  3. washrinsed with triethylamine/ethyl acetate (1/4)
  4. concentrationThe filtrate was concentrated under vacuo
  5. customthe residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-818ec0c81053432b97b5eee30671056f
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Linked notes

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