Sodium hydride → HCID 57659596, compound

HRID 1172588Notes

Reaction equation

HRID 1172588 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][CH2:14]O)=[CH:11][C:10]([CH3:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[K]>CN(C=O)C>[CH2:1]([N:8]1[C:12]([CH2:13][CH2:14][N:23]2[C:19](=[O:29])[C:20]3[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:22]2=[O:24])=[CH:11][C:10]([CH3:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 24194345Phthalimide potassium saltHCID 57659574HCID 57659574, compound

Product 1

HCID 57659596HCID 57659596, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

2-(2-Benzyl-5-methyl-2H-pyrazol-3-yl)-ethanol (848 mg, 3.92 mmol) was dissolved in DMF (21 ml) and cooled to −20° C. followed by the addition of sodium hydride (218 mg, 5.02 mmol). Stirring was continued at rt for 30 minutes. The reaction mixture was again cooled to −20° C. and toluene-4-suofonyl chloride (pTs-Cl, 966 mg, 5.02 mmol) was added. The cooling bath was removed and stirring was continued for 2 h at rt and 30 minutes at 50° C. followed by the addition of potassium phthalimid (1.7 g, 9.2 mmol). Stirring at 50° C. was continued for 2 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was taken up in DCM (30 ml) filtered again and the filtrate was washed with water (30 ml). The phases were separated. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by preparative HPLC to give 80 mg (6%) of 2-[2-(2-benzyl-5-methyl-2H-pyrazol-3-yl)-ethyl]-isoindole-1,3-dione. LC-MS: tR=0.95 min; [M+H]+=346.31.

Workup

  1. temperatureThe reaction mixture was again cooled to −20° C.
  2. customThe cooling bath was removed
  3. stirringstirring
  4. waitwas continued for 2 h at rt and 30 minutes at 50° C.
  5. stirringStirring at 50° C.
  6. waitwas continued for 2 h
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. filtrationfiltered again
  10. washthe filtrate was washed with water (30 ml)
  11. customThe phases were separated
  12. dry with materialThe organic phase was dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-0aa8b38e3ff1489faa3a9f41f2099ed6
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

Loading…