Water → 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

HRID 1815916Notes

Reaction equation

HRID 1815916 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[N:8]=[CH:7]2)([O-:3])=[O:2].[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH2:7]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 5642092-(Bromomethyl)pyridine

Product 2

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazoleHCID 22496150HCID 22496150, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitroindazole (2 g, 12.3 mmol) in DMF (20 mL) was added K2CO3 (5.1 g, 36.8 mmol) and 2-(bromomethyl)-pyridine (2.2 g, 13.5 mmol). The resulting mixture was stirred at RT for 3.5 days, then poured into 100 mL of water. The resulting slurry was filtered, rinsed once with water and dried in vacuo giving a solid. The crude material was purified by chromatography (SiO2, elution with 3:1 EtOAc-hexanes followed by EtOAc followed by 7:1 CH2C2—MeOH) giving 5-nitro-1-pyridin-2-ylmethyl-1H-indazole and 5-nitro-2-pyridin-2-ylmethyl-1H-indazole.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washrinsed once with water
  3. customdried in vacuo
  4. customgiving a solid
  5. customThe crude material was purified by chromatography (SiO2, elution with 3:1 EtOAc-hexanes followed by EtOAc followed by 7:1 CH2C2—MeOH)

Sources & evidence

ORD record
ord-c6449114ba7c4c53b7dc2e08aed8a162
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

Loading…