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

HRID 975020Notes

Reaction equation

HRID 975020 reaction equation
[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]

Participants

7

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cc4cb2874c0041e5b11bd206bbecca49
Source dataset
uspto-grants-1997_03
Patent number
US05607951

Reaction notes

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