Bromocyclopentane → HCID 59597439, compound

HRID 2265399Notes

Reaction equation

HRID 2265399 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:25][C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH:31]1(Br)[CH2:35][CH2:34][CH2:33][CH2:32]1.[H-].[Na+]>CN(C=O)C>[CH:31]1([N:28]2[CH:27]=[C:26]([CH2:25][N:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=3)[C:11]([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[CH2:16][CH2:15][CH2:14]3)=[O:12])[CH:30]=[N:29]2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 59597365HCID 59597365, compound

Product 1

HCID 59597439HCID 59597439, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-Isopropylphenyl)-7-methoxy-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.44 g) and cyclopentyl bromide (0.12 mL) were dissolved in DMF (5 mL), and sodium hydride (0.09 g) was added under ice-cooling. The mixture was stirred at the same temperature for 30 min and then at room temperature for 5 hr. The reaction mixture was concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-[(1-cyclopentylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.38 g).

Workup

  1. temperaturecooling
  2. waitat room temperature for 5 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompartitioned between water and ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aaa1c3d6fb65454f9ee193e4b220cc03
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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