Sodium hydride → HCID 22718092, compound

HRID 2227726Notes

Reaction equation

HRID 2227726 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:17]=[CH:16][NH:15][N:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1>C1COCC1>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:17]=[CH:16][N:15]([C:23]4[N:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[N:14]=3)=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 178505882HCID 178505882, compound

Product 1

HCID 22718092HCID 22718092, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(4-fluorophenoxy)phenyl]-1H-pyrazole (930 mg, 3.66 mmol) in 15 mL of dry THF was slowly added 240 mg (6.00 mmol) of NaH. After stirring at room temperature for 20 minutes, 500 mg (4.15 mmol) of 2-chloropyrimidine was added in one portion. The reaction was allowed to stir overnight at room temperature and concentrated to dryness. The residue was dissolved in CHCl3 and subjected to flash chromatography. Elution with 3:2 hexane/EtOAc gave 994 mg of the title compound as a solid, mp 123-125° C. 1H NMR (CDCl3): δ8.77 (d, 2H, J=4.8 Hz), 8.65 (d, 1H, J=3.0 Hz), 7.95 (d, 2H, J=8.7 Hz), 7.20 (t, 1H, J=4.9 Hz), 7.07-6.98 (m, 5H), 6.78 (d, 1H, J=3.0 Hz).

Workup

  1. stirringto stir overnight at room temperature
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in CHCl3
  4. washElution with 3:2 hexane/EtOAc

Sources & evidence

ORD record
ord-99a9ab1fa0ef4b6b84550120119f2abd
Source dataset
uspto-grants-2002_07
Patent number
US06414011B1

Reaction notes

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