Potassium Carbonate → HCID 22036562, compound

HRID 1790098Notes

Reaction equation

HRID 1790098 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(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23]Cl>CN(C=O)C>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[N:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 180574-NitroindazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 22036562HCID 22036562, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-nitroindazole (2.0 g, 12 mmol) and potassium carbonate (5.1 g 37 mmol) in DMF (40 mL) was stirred for 30 minutes, after which 2-(dimethylamino)ethylchloride hydrochloride (2.7 g 18 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and filtered through a plug of silica gel, which was rinsed with triethylamine/ethyl acetate (1/4). The combined filtrate was concentrated under reduced pressure and purified by Flash Chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound (1.6g, 50% yield). 1H NMR (300 MHz, DMSO-d6) ppm 2.74(t, J=6.44, 2H), 3.31 (s, 6H), 4.63 (t, J=6.44, 2H), 7.64 (m, 1H), 8.16 (m, 1H), 8.30 (m, 1H), 8.51(m, 1H); MS (DCI/NH3) m/z 235 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a plug of silica gel, which
  3. washwas rinsed with triethylamine/ethyl acetate (1/4)
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. custompurified by Flash Chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-4f4be7aff6c1435cb2399bf62f629f25
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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