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

HRID 1790082Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

4-Nitroindazole (3.00 g, 18.4 mmol) and potassium carbonate (7.50 g, 54.4 mmol) in 60 mL of DMF was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (4.80 g 28.4 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. The silica gel was rinsed with triethylamine/ethyl acetate (1/4), the combined filtrate was concentrated under reduced pressure and the residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.60 (m, 4H), 2.45 (m, 4H), 2.92 (t, 2H, J=6.45), 4.65 (t, 2H, J=6.45), 7.65 (m, 1H), 8.10 (m, 1H), 8.30 (m, 1H), 8.52 (s, 1H); MS (DCI/NH3) m/z 261 [M+H]+.

Workup

additionwas added
temperaturecooled to room temperature
filtrationfiltered through a plug of silica gel
washThe silica gel was rinsed with triethylamine/ethyl acetate (1/4)
concentrationthe combined filtrate was concentrated under reduced pressure
customthe residue purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30)

Sources & evidence

ORD record: ord-2022f7ff30e3468aa8447d7af54d0c16
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071182B2

Reaction notes

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