Potassium Carbonate → HCID 22138902, compound

HRID 1825832Notes

Reaction equation

HRID 1825832 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]([CH:12]=1)=[N:10][N:9]([CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH:8]=2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 242396-NitroindazoleHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 22138902HCID 22138902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6-Nitroindazole (2.00 g, 12.3 mmol) was treated with potassium carbonate (5.00 g 36.2 mmol) in N,N-dimethylformamide (40 mL) for 30 minutes and then 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (3.20 g 18.8 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours, then cooled to room temperature. The reaction mixture was filtered through a plug of silica gel and rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 1.65 (m, 4H) 2.48 (m, 4H), 3.00 (t, 2H, J=6.44), 4.64 (t, 2H, J=6.44), 7.80 (m, 1H), 7.97 (m, 1H), 8.62 (s, 1H), 8.68 (s, 1H); MS (DCI/NH3) m/z 261 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture was filtered through a plug of silica gel
  3. washrinsed with triethylamine/ethyl acetate (1/4)
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record
ord-77b250971d424e5fade3bca122e86e90
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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