Sodium hydride → 3-Bromo-1-(2-ethoxy naphthoyl)-7-azaindole

HRID 1820895Notes

Reaction equation

HRID 1820895 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[CH2:13]([O:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]=1[C:26](Cl)=[O:27])[CH3:14]>CN(C)C=O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:26]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=[CH:25][C:16]=2[O:15][CH2:13][CH3:14])=[O:27])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1086791-Naphthalenecarbonyl chloride, 2-ethoxy-HCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497589133-Bromo-1-(2-ethoxy naphthoyl)-7-azaindoleYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-7-azaindole (500 mg, 2.0 mmol) 3 was dissolved in N,N-dimethylformamide (50 mL) and sodium hydride (210 mg, 5.3 mmol, 60% dispersion in mineral oil) and 2-Ethoxy-naphthalene-1-carbonyl chloride (710 mg, 3.0 mmol) were added. The reaction mixture was stirred at ambient temperature for 30 min, cast into ice water (100 mL) and extracted into ethyl acetate. The organic portion was dried with anhydrous magnesium sulfate, filtered and the filtrate concentrated. Purification via column chromatography (10% Ethyl acetate in hexanes) provided the desired product 85 (800 mg, 80%).

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe organic portion was dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customPurification via column chromatography (10% Ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-714e4e7384fb4777baa087d810809a8a
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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