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

HRID 975020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975020
[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-cc4cb2874c0041e5b11bd206bbecca49
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607951

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