Dimethylamine → 1-(3-(N,N-dimethylamino)propyl)-6-(3-thienyl)-1H-indazole

HRID 988110Notes

Reaction equation

HRID 988110 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[CH:12]=2)[CH:7]=[N:6]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH3:27][NH:28][CH3:29]>C(#N)C.ClCCl>[CH3:27][N:28]([CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[CH:12]=2)[CH:7]=[N:6]1)[CH3:29]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18007587HCID 18007587, compound

Product 1

HCID 180075481-(3-(N,N-dimethylamino)propyl)-6-(3-thienyl)-1H-indazoleYield 95.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-chloropropyl)-6-(3-thienyl)-1H-indazole (27.8 mg, 0.10 mmol), potassium iodide (155 mg, 1 mmol), potassium carbonate (130 mg, 1 mmol), and dimethylamine (2M in THF, 0.5 mL, 1 mmol) in acetonitrile (0.5 mL) was heated at reflux overnight. After cooling to room temperature, the mixture was diluted with dichloromethane (5 mL) and filtered through a small plug of alumina to remove the solids, rinsing with dichloromethane (10 mL). After removal of the solvent in vacuo, flash chromatography (silica gel, 2.5-5% 2M methanolic ammonia in dichloromethane) yielded 1-(3-(N,N-dimethylamino)propyl)-6-(3-thienyl)-1H-indazole (27.2 mg, 95%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationfiltered through a small plug of alumina
  4. customto remove the solids
  5. washrinsing with dichloromethane (10 mL)
  6. customAfter removal of the solvent in vacuo, flash chromatography (silica gel, 2.5-5% 2M methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-f14d0db0877a444f9460088342111355
Source dataset
uspto-grants-2003_10
Patent number
US06635639B2

Reaction notes

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