Sodium hydride → 3-(4-methoxybenzyl)-1H-pyrrolo[3,2-f]quinoline-1,2(3H)-dione

HRID 1407489Notes

Reaction equation

HRID 1407489 reaction equation
[C:1]1(=[O:15])[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3.[H-].[Na+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:3]2[C:4]3[C:5](=[C:6]4[C:11](=[CH:12][CH:13]=3)[N:10]=[CH:9][CH:8]=[CH:7]4)[C:1](=[O:15])[C:2]2=[O:14])=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 213070621H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dione

Product 1

HCID 685988063-(4-methoxybenzyl)-1H-pyrrolo[3,2-f]quinoline-1,2(3H)-dioneYield 82.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1H-pyrrolo[3,2-f]quinoline-1,2(3H)-dione (Bramson, H. N. et al. J. Med. Chem. 2001, 44 (25):4339-4358) (0.15 g, 0.76 mmol) in dry N,N-dimethylformamide (10 mL) was added sodium hydride (60% in mineral oil, 0.04 g, 0.98 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 1 h and 4-methoxybenzyl bromide (0.16 mL, 1.1 mmol) was added. The mixture was stirred at ambient temperature for 16 h and was diluted with water (100 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with a 50% to 65% gradient of ethyl acetate in hexanes to afford 3-(4-methoxybenzyl)-1H-pyrrolo[3,2-f]quinoline-1,2(3H)-dione (0.20 g, 82%) as a red solid: MS (ES+) m/z 319.0 (M+1).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 16 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with a 50% to 65% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e89b63190f2e4137879cc68d514e1cce
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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