Sodium hydride → [3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-naphthalen-1-yl)-methanone

HRID 1820889

Reaction equation

HRID 1820889 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH2:22]([O:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]=1[C:35](Cl)=[O:36])[CH3:23]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:35]([C:26]3[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:33]=[CH:34][C:25]=3[O:24][CH2:22][CH3:23])=[O:36])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1086791-Naphthalenecarbonyl chloride, 2-ethoxy-HCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 11583285[3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-naphthalen-1-yl)-methanoneYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine 1 (638 mg, 2.51 mmole) was dissolved in DMF (30 mL) and sodium hydride (60% dispersion in mineral oil, 100 mg, 2.50 mmole) was added in small portions to the reaction mixture. After stirring for 30 minutes, 2-ethoxy-1-naphthoyl chloride (646 mg, 2.76 mmole) was added and the reaction was stirred for 4 hours. The reaction mixture was poured into 200 mL of ice water and was extracted with ethyl acetate. The organic layer was washed with saturated bicarbonate solution followed by saturated potassium hydrogen sulfate and then brine. The resulting solution was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate:hexanes) to yield 800 mg (70%) of the titled compound as a white solid MS(ESI) [M+H+]+=453.06.

Workup

  1. stirringthe reaction was stirred for 4 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated bicarbonate solution
  4. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-57c9ad57aeee40adb993f07128b8d86d
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Linked notes

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