Aluminium lithium hydride → HCID 69235167, compound

HRID 1593653Notes

Reaction equation

HRID 1593653 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([C:17]([NH2:19])=O)[CH2:8][C:7]2=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([CH2:17][NH2:19])[CH2:8][C:7]2=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69236140HCID 69236140, compound

Product 1

HCID 69235167HCID 69235167, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 6-(trifluoromethoxy)-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide of Step 3 (1.22 g, 4.09 mmol) in anhydrous tetrahydrofuran kept under nitrogen, was added via syringe a 1M solution of lithium aluminum hydride in terahydrofuran (8.18 mmol). The pale yellow suspension was heated at 70° C. for 1 hour, allowed to cool to room temperature and then placed in an ice water bath. Under vigorous stirring the mixture was quenched with ethyl acetate, followed by a saturated aqueous solution of Rochelle salt. The slurry was extracted with ethyl acetate, the extracts were washed with brine and dried over anhydrous magnesium sulfate. Removal of the solvent provided a solid residue that was purified by chromatography over silica Merck 60 using a 2% to 10% gradient of methanolic ammonia in dichloromethane to provide the title compound as a white solid (0.946 g, 81.6%), m.p. 148-150° C. MS [(+)ES, m/z]: 285.1 [M+H]+. MS [(−)ES, m/z]: 283.1 [M−H]−. HRMS [(+)ESI, m/z]: 285.1212 [M+H]+. Calc'd for C14H16F3N2O: 285.1214. HPLC: Chromolith Monolith column, 0.46×10 cm, gradient of acetonitrile in water (0.01% TFA), 4 mL/min, detection at 280 nm; Rt 1.6 min.

Workup

  1. temperatureto cool to room temperature
  2. customplaced in an ice water bath
  3. customwas quenched with ethyl acetate
  4. extractionThe slurry was extracted with ethyl acetate
  5. washthe extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the solvent
  8. customprovided a solid residue that
  9. customwas purified by chromatography over silica Merck 60 using a 2% to 10% gradient of methanolic ammonia in dichloromethane

Sources & evidence

ORD record
ord-6f87ab77b9d24d8681777ee2226a5876
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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