Hydrochloric Acid → HCID 68635091, compound

HRID 1802811Notes

Reaction equation

HRID 1802811 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15]CC)=[O:14])=[CH:9]2)([O-])=O.[O:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].Cl>CO.O1CCCC1.[Pd].O.ClCCCl>[O:18]1[CH2:23][CH2:22][CH:21]([NH:1][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:12]=2[NH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9]3)[CH2:20][CH2:19]1

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 250407Ethyl 7-nitro-1H-indole-2-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68635091HCID 68635091, compoundYield 76%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-nitroindole-2-carboxylate (2.5 g, 10.7 mmol) was dissolved in methanol (50 ml). 10% Pd/C (200 mg) was added, and the mixture was stirred for 1 h under hydrogen gas. The mixture was filtered though celite, and the filtrate was distilled under reduced pressure. The distillate was dissolved 1,2-dichloroethane (50 ml), and tetrahydro-4H-pyran-4-one (1.3 ml, 12.8 mmol) and sodium triacetoxyborohydride (3.4 g, 16.1 mmol) were added. The mixture was stirred for 8 h at room temperature. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and concentrated. The residue was purified by column chromatography. Thus obtained compound was dissolved in methanol (50 ml) and tetrahydrofuran (50 ml), 1N-sodium hydroxide (43 ml, 42.8 mmol) was added, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to give the title compound (2.1 g, Yield 76%).

Workup

  1. filtrationThe mixture was filtered though celite
  2. distillationthe filtrate was distilled under reduced pressure
  3. additionwere added
  4. stirringThe mixture was stirred for 8 h at room temperature
  5. additionwas added
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. distillationThe filtrate was distilled under reduced pressure
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography
  12. dissolutionThus obtained compound was dissolved in methanol (50 ml)
  13. stirringthe mixture was stirred for 8 h at room temperature
  14. extractionthe mixture was extracted with ethyl acetate
  15. dry with materialdried over anhydrous magnesium sulfate
  16. filtrationfiltered
  17. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-fc55554952aa42c08e1a255d5dc80379
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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