Sodium hydride → HCID 23594010, compound

HRID 1612060Notes

Reaction equation

HRID 1612060 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[C:14]3[C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[CH:6]=[C:5]2[CH2:20][CH2:21][CH2:22][CH2:23][C:4]=12.[H-].[Na+]>CN(C=O)C>[CH2:23]([N:8]1[C:7]2[CH:6]=[C:5]3[CH2:20][CH2:21][CH2:22][CH2:23][C:4]3=[C:3]([O:2][CH3:1])[C:15]=2[C:14]2[C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=[CH:10][C:9]1=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:15][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23594011HCID 23594011, compound

Product 1

HCID 23594010HCID 23594010, compoundYield 132.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.155 g, 0.5 mM) in 5 mL DMF was added to a 60% NaH mineral oil dispersion (0.04 g, 1.0 mM, washed twice with hexane) at room temperature. Following cessation of gas evolution, benzyl bromide (0.067 mL, 0.094 g, 0.55 mM) was added and the mixture stirred at room temperature for 3 h. The mixture was diluted with ethyl acetate and H2O, the solvent layers separated, and the aqueous layer extracted with ethyl acetate (4×25 mL). The combined ethyl acetate extracts were washed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and triturated with hexanes. The resultant tan solid was dried in vacuo, and purified by column chromatography on silica gel (elution with 9:1 toluene/ethyl acetate) to afford 0.133 g (66%) of the title compound 5-benzyl-11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as an off-white foam (MP 144–146° C., MW 399.49).

Workup

  1. washwashed twice with hexane) at room temperature
  2. additionwas added
  3. additionThe mixture was diluted with ethyl acetate and H2O
  4. customthe solvent layers separated
  5. extractionthe aqueous layer extracted with ethyl acetate (4×25 mL)
  6. washThe combined ethyl acetate extracts were washed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customtriturated with hexanes
  11. customThe resultant tan solid was dried in vacuo
  12. custompurified by column chromatography on silica gel (elution with 9:1 toluene/ethyl acetate)

Sources & evidence

ORD record
ord-2075fd2e90c24686b52844a52265ccf7
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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