Water → HCID 90308901, compound

HRID 2283696Notes

Reaction equation

HRID 2283696 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-])=O.[OH2:13]>CN(C=O)C>[O:13]1[CH2:6][CH2:5][C@@H:4]([N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=3[CH:6]=[CH:7]2)[CH2:12]1

Participants

4

Reactant 2

HCID 962WaterHCID 1457664-Nitro-1H-indole

Product 1

HCID 90308901HCID 90308901, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (2.5 g) and (S)-tetrahydrofuran-3-yl methanesulfonate obtained in the above-described Step (1.01 g) were added to a solution of 4-nitro-1H-indole (980 mg) in DMF (10 mL), and the reaction solution was stirred at 100° C. for 24 hours. Water was added to the reaction solution, the reaction solution was extracted with ethyl acetate twice, and then washed successively with water and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate). THF (10 mL) was added to the resultant residue, 10% palladium on carbon (100 mg) was added, and the reaction solution was stirred under hydrogen atmosphere at room temperature for 14 hours. The insolubles were filtrated with celite, and the solvent was evaporated under vacuum. Thereafter, the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 1-((R)-tetrahydrofuran-3-yl)-1H-indol-4-amine as a white solid.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate twice
  2. washwashed successively with water
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)
  6. additionTHF (10 mL) was added to the resultant residue, 10% palladium on carbon (100 mg)
  7. additionwas added
  8. stirringthe reaction solution was stirred under hydrogen atmosphere at room temperature for 14 hours
  9. filtrationThe insolubles were filtrated with celite
  10. customthe solvent was evaporated under vacuum
  11. customThereafter, the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f8296f7d99274dd79eac2aa95e561a69
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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