Water → HCID 11660224, compound

HRID 735420Notes

Reaction equation

HRID 735420 reaction equation
Cl[C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]([F:14])([F:13])[F:12].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.O>CS(C)=O>[C:15]1([N:3]2[C:2]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[C:10]3[C:5]([C:6]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:8]=[CH:9]3)=[N:4]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 67021058HCID 67021058, compound

Product 1

HCID 11660224HCID 11660224, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

3-Chloro-2-phenyl-7-trifluoromethyl-2H-indazole (21 mg, 0.07 mmol, compound of formula (XI)) was dissolved in 0.5 ml of DMSO and 100 μl of piperidine (1 mmol) were added. The reaction mixture was stirred overnight at 110° C. After cooling to room temperature, 10 volumes of water were added. The supernatant was removed and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate, 50:50, as eluent) to provide the title compound as a white solid (9 mg, 37%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe supernatant was removed
  3. customthe residue was purified by column chromatography on silica (n-heptane/ethyl acetate, 50:50, as eluent)

Sources & evidence

ORD record
ord-41b0a19efe6748ea8270ab79fd5b6a36
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

Loading…