Water → 4-chloro-1-(4-fluorobenzyl)-1H-pyrazolo[4,3-c]pyridine

HRID 2097001Notes

Reaction equation

HRID 2097001 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:16][C:15]3[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 468356374-chloro-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 581107234-chloro-1-(4-fluorobenzyl)-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-chloro-1H-pyrazolo[4,3-c]pyridine (60 mg, 0.40 mmol) in 2 ml DMF was added 4-Fluorobenzylbromide (0.060 ml, 0.48 mmol) then add NaH (20 mg, 0.4 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 38 mg of major isomer A and 15 mg of minor isomer B.

Workup

  1. extractionextract three times with EtOAc
  2. washPool all organics and wash one time with brine
  3. dry with materialthen dry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate to dryness
  6. customThe residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50)
  7. customto provide 38 mg of major isomer A and 15 mg of minor isomer B

Sources & evidence

ORD record
ord-4718b4f4e2984d73931017e1e5bbb7f1
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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