Phosgene → 5-sulfonylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

HRID 745003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745003
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].C(N(CC)CC)C.[C:25](Cl)(Cl)=[O:26].[S:29](Cl)(Cl)(=[O:31])=[O:30]>C(#N)C>[C:25](=[N:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17])=[O:26].[S:29](=[N:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17])(=[O:31])=[O:30]

Komponenten

7

Edukt 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Produkt 2

HCID 199702555-sulfonylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indoleHCID 867497155-carbonylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of (R)-5-amino-3-(N-methylpyrrolidin-2-ylmethyl)indole (0.229 g, 1.00 mmol) and triethylamine (0.21 mL, 1.5 mmol, 1.5 eq) in anhydrous acetonitrile (3 mL) at 0° C. under nitrogen was added the appropriate carbonyl chloride or sulfonyl chloride (1.5 mmol, 1.5 eq). The resulting reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was then evaporated under reduced pressure, and the residue was column chromatographed using silica gel (approximately 25 g) and elution with an appropriate solvent system afforded the appropriate 5-carbonylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole or 5-sulfonylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customchromatographed
  4. washsilica gel (approximately 25 g) and elution with an appropriate solvent system

Quellen und Nachweise

ORD-Eintrag
ord-23b3d01c411d440db14e637c7680a5c2
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559246

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