Sodium hydride → 2-[4-[3-(3-Pyridinyl)-1h-pyrazol-1-yl]butyl]-1h-isoindole-1,3(2h)-dione

HRID 432942Notes

Reaction equation

HRID 432942 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:2]1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29]>CN(C=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3]2[CH:4]=[CH:5][N:1]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[N:2]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimideHCID 178420771HCID 178420771, compound

Product 1

HCID 121166052-[4-[3-(3-Pyridinyl)-1h-pyrazol-1-yl]butyl]-1h-isoindole-1,3(2h)-dioneYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15.45 g of 3-(1H pyrazol-3-yl)-pyridine prepared as indicated in CA 68 P 95812 g (1968) is introduced dropwise over 1 hour while maintaining the temperature below 30° C. or equal to 30° C. into a mixture of 20 ml of DMF and 6.13 g of sodium hydride. A solution of 29.90 g of 2-(4-bromobutyl)-1H -isoindole-1,3(2H)-dione and 110 ml of DMF is added dropwise. The reaction medium is agitated for 30 minutes at ambient temperature, followed by concentrating, pouring into 300 ml of water cooled down to 10° C., extracting with ethyl acetate, washing with water, drying, filtering and concentrating. The residue is taken up in methylene chloride, followed by drying, filtering and concentrating. 35.87 of a product is obtained which is crystallized from ethyl ether, dried, washed with water and dried. 22.93 g of sought product is obtained.

Workup

  1. additionis introduced dropwise over 1 hour
  2. temperaturewhile maintaining the temperature below 30° C.
  3. concentrationby concentrating
  4. additionpouring into 300 ml of water
  5. temperaturecooled down to 10° C.
  6. extractionextracting with ethyl acetate
  7. washwashing with water
  8. customdrying
  9. filtrationfiltering
  10. concentrationconcentrating
  11. customby drying
  12. filtrationfiltering
  13. concentrationconcentrating
  14. custom35.87 of a product is obtained which
  15. customis crystallized from ethyl ether
  16. customdried
  17. washwashed with water
  18. customdried

Sources & evidence

ORD record
ord-734a0581948b49d498e0c10ce68f6c88
Source dataset
uspto-grants-2003_12
Patent number
US06664398B2

Reaction notes

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