Pyrazole → HCID 52141936, compound

HRID 2361636Notes

Reaction equation

HRID 2361636 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1>CS(C)=O.C(Cl)Cl>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 52141936HCID 52141936, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of pyrazole (300 mg, 4.4 mmol) in DMSO (2 ml) at RT was added NaH (176 mg, 4.4 mmol, 60% in mineral oil) portionwise. The mixture was stirred at RT for 1 h and 4-fluorobenzylbromide (1.0 g, 5.3 mmol) added dropwise. The mixture was stirred at 50° C. for 0.5 h, cooled to RT and diluted with DCM (20 ml). The resulting mixture was filtered and the filtrate washed with brine (10 ml). The organic layer was then dried (NaSO), filtered and concentrated at reduced pressure. Purification by silica flash column chromatography (eluting with DCM/MeOH 95:5) provided the title compound as colourless oil (650 mg, 84%).

Workup

  1. stirringThe mixture was stirred at 50° C. for 0.5 h
  2. temperaturecooled to RT
  3. filtrationThe resulting mixture was filtered
  4. washthe filtrate washed with brine (10 ml)
  5. dry with materialThe organic layer was then dried (NaSO)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customPurification
  9. washby silica flash column chromatography (eluting with DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-18444a0bb44c4355b7507f4250dccab9
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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