3-Bromopentane → HCID 25128637, compound

HRID 424610Notes

Reaction equation

HRID 424610 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH:20]=[N:19][NH:18][C:17](=[O:21])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:24][CH2:25][CH:26](Br)[CH2:27][CH3:28]>CN(C)C=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH:20]=[N:19][N:18]([CH:26]([CH2:27][CH3:28])[CH2:25][CH3:24])[C:17](=[O:21])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 25133793HCID 25133793, compound

Product 1

HCID 25128637HCID 25128637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-(3-(cyclopentyloxy)-4-methoxyphenyl)pyridazin-3-one prepared in Working Example 5, sodium hydride was added and stirred for 1 hour. Then, 3-pentylbromide dissolved in dimethylformamide was added dropwise and stirred for 18 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The residue that had been filtered and concentrated was purified by flash chromatography to obtain the title compound.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. stirringstirred for 18 hours
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe residue that had been filtered
  9. concentrationconcentrated
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e2dec631959f4c6bb3a5533cc45eb1ee
Source dataset
uspto-grants-2012_01
Patent number
US08106053B2

Reaction notes

Loading…