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

HRID 271699Notes

Reaction equation

HRID 271699 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-5b94af4bbe6c4657a23fd451866e8a47
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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