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

HRID 744145ノート

反応式

HRID 744145 の反応式
[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]

参加物

7

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ff2688cae71f41ac874a4027683f8001
出典データセット
uspto-grants-1996_09
特許番号
US05559129

反応ノート

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