Potassium Carbonate → 5-Nitro-2-(2-(pyrrolidin-1-yl)ethyl)-2H-indazole

HRID 1916664Notes

Reaction equation

HRID 1916664 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].[N+:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][N:23]=[CH:22]2)([O-:18])=[O:17]>C(#N)C>[N+:16]([C:19]1[CH:27]=[CH:26][C:25]2[C:21](=[CH:22][N:23]([CH2:3][CH2:4][N:5]3[CH2:9][CH2:8][CH2:7][CH2:6]3)[N:24]=2)[CH:20]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 221389045-Nitro-2-(2-(pyrrolidin-1-yl)ethyl)-2H-indazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.5 g (62.0 mmol) 1-(2-chloroethyl)-pyrrolidine hydrochloride and 12.9 g (93.0 mmol) K2CO3 are added successively to a solution of 5.00 g (31.0 mmol) 5-nitroindazole in 100 mL acetonitrile. The reaction solution is stirred for 2 h at RT and refluxed for a further 5 h. After the solution has cooled the insoluble salts are filtered off and the solvent is eliminated i.vac. The residue is taken up in EtOAc and water. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. A 4:1 mixture of 5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole and 5-nitro-2-(2-pyrrolidin-1-yl-ethyl)-2H-indazole is obtained. The purification is carried out by column chromatography on Alox (PE/EtOAc 3:2).

Workup

  1. temperaturerefluxed for a further 5 h
  2. temperatureAfter the solution has cooled the insoluble salts
  3. filtrationare filtered off
  4. dry with materialThe organic phase is dried over MgSO4
  5. additionA 4:1 mixture of 5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Sources & evidence

ORD record
ord-36d3bb82adf84e00976ec3ad6c4152da
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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