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

HRID 1820893Notes

Reaction equation

HRID 1820893 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[NH:19][CH:20]=[CH:21][C:14]=23)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[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]>CCCCCC.O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19]([C:35]([C:26]4[C:27]5[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:33]=[CH:34][C:25]=4[O:24][CH2:22][CH3:23])=[O:36])[CH:20]=[CH:21][C:14]=23)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1086791-Naphthalenecarbonyl chloride, 2-ethoxy-HCID 119990244-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57891669[4-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-naphthalen-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 39.9 mg, 0.997 mmol) was washed with hexane and put under an atmosphere of nitrogen, and 1 mL of tetrahydrofuran was added. 4-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (50, 195 mg, 0.767 mmol) in tetrahydrofuran (6.2 mL) was added, and the resulting mixture was stirred for 10 minutes at room temperature. 2-ethoxy naphthoyl chloride (202 mg, 0.844 mmol) in tetrahydrofuran was added. After two hours, the reaction was quenched with water, and the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded the crude material, which was purified by column chromatography (35-60% ethyl acetate in hexane) to yield the desired product in light yellow solid (48, 262 mg, 0.579 mmol). MS(ESI) [M+H+]+=453.2.

Workup

  1. waitAfter two hours
  2. customthe reaction was quenched with water
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration under reduced pressure
  8. customafforded the crude material, which
  9. customwas purified by column chromatography (35-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bfe3f6f536834519b8ea5f76fe900b37
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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