Trityl chloride → 6-chloro-3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 571375Notes

Reaction equation

HRID 571375 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][NH:10][C:4]=2[CH:3]=1.[H-].[Na+].[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][N:10]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 768471656-Chloro-3-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 895258266-chloro-3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridineYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-3-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridine (1 g, 4.04 mmol) was dissolved in DMF (20 mL) and cooled to 0° C. Sodium hydride (0.242 g, 6.06 mmol) was then added and the reaction mixture stirred for one hour. Trityl chloride (1.351 g, 4.85 mmol) was then added and the reaction mixture warmed to room temperature and stirred for 1.5 hours. The reaction mixture was diluted with water and stirred at 0° C. for one hour to promote perception. The solid was filtered and rinsed with water. The solid was diluted with DCM and concentrated in vacuo while loading onto silica gel. The residue was purified by flash chromatography (2-30% EtOAc/isohexane) to give 6-chloro-3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine (1.63 g, 3.33 mmol, 82%). MS ESI calc'd. For C31H21ClFN3 [M+1]+ 490, found 490.

Workup

  1. temperaturethe reaction mixture warmed to room temperature
  2. stirringstirred for 1.5 hours
  3. stirringstirred at 0° C. for one hour
  4. filtrationThe solid was filtered
  5. washrinsed with water
  6. additionThe solid was diluted with DCM
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (2-30% EtOAc/isohexane)

Sources & evidence

ORD record
ord-d2a6f09b87d14c51a78e53043bce8278
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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