Potassium Carbonate → HCID 2768024, compound

HRID 1825821Notes

Reaction equation

HRID 1825821 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]([CH3:25])[CH3:24]>CN(C)C=O>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][N:8]1[CH:7]=[C:6]2[C:10]([CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5]2)=[N:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 2768024HCID 2768024, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-Nitroindazole (1.00 g, 6.13 mmol) was dissolved in 20 mL of N,N-dimethylformamide and potassium carbonate (2.50 g, 18.1 mmol) was added. The mixture was stirred for 30 minutes and then (2-chloro-ethyl)-dimethyl-amine hydrochloride (1.32 g 9.16 mmol) was added. The reaction 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 in vacuo and the residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30). 1H NMR (300 MHz, DMSO-d6) ppm 2.18 (s, 6H), 2.81 (t, 2H, J=6.44), 4.60 (t, 2H, J=6.44), 7.78 (m, 1H), 8.00 (m, 1H), 8.82 (s, 1H), 8.89 (m, 1H); MS (DCI/NH3) m/z 235 [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 in vacuo
  5. customthe residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-609977b5620143fdbbf236bca3965eb6
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

Loading…