3-Bromopentane → HCID 117988358, compound

HRID 2205977Notes

Reaction equation

HRID 2205977 reaction equation
[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].Br[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17]>CN(C=O)C>[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 534125573-Bromo-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 117988358HCID 117988358, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (1.00 g) in DMF (30 mL) was added sodium hydride (60% dispersion in mineral oil, 0.207 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 3-bromopentane (0.851 g), and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate to ethyl acetate) to give the title compound (90.5 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate to ethyl acetate)

Sources & evidence

ORD record
ord-27c98267deb94207b4f73622c2797453
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…