Potassium Carbonate → 3-chloro-4-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

HRID 1790158Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-chloro-4-nitro-1H-indazole (0.550 g, 2.79 mmol) was treated with potassium carbonate (1.20 g 8.70 mmol) in DMF (10 mL) for 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (0.710 g, 4.20 mmol) was added. The mixture was heated to 50° 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. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.60 (m, 4H), 2.46 (m, 4H), 2.90 (t, 2H, J=6.44), 4.61 (t, 2H, J=6.44), 7.66 (m, 1H), 7.98 (m, 1H), 8.25 (m, 1H); MS (DCI/NH3) m/z 261 [M+H]+.

Workup

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

Sources & evidence

ORD record: ord-8f1ce3ca17d440acba30939cbb5f2814
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071182B2

Reaction notes

Loading…