Potassium Carbonate → HCID 22036566, compound

HRID 1790166Notes

Reaction equation

HRID 1790166 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 178526490HCID 178526490, compound

Product 1

HCID 22036566HCID 22036566, compoundYield 133.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-bromo-5-nitro-1H-indazole (1.8 g, 7.6 mmol) and potassium carbonate (3.1 g 22 mmol) in DMF (20 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine (0.71 g, 4.2 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature, 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 (1.9 g, 76%). 1H NMR (300 MHz, DMSO-d6) ppm 1.60 (m, 4H), 2.46 (m, 4H), 2.90 (t, 2H, J=6.44), 4.60 (t, J=6.44, 2H), 8.00 (m, 1H), 8.30 (m, 1H), 8.48 (m, 1H); MS (DCI/NH3) m/z 339 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-f5e25737fd3846fd89334f3669445254
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

Loading…