Pyridine → HCID 19696325, compound

HRID 863679Notes

Reaction equation

HRID 863679 reaction equation
C([O:4][CH2:5][CH2:6][CH:7]1[CH2:36][CH2:35][N:10]2[C:11]3[C:16]([C:17]([C:18]4[C:19](=[O:34])[O:20][C:21](=O)[C:22]=4[C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]([CH3:32])[CH:24]=4)=[C:9]2[CH2:8]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)(=O)C.[CH3:37][S:38]([O:41]S(C)(=O)=O)(=O)=[O:39].[N:46]1C=CC=CC=1>ClCCl>[CH3:37][S:38]([O:4][CH2:5][CH2:6][CH:7]1[CH2:36][CH2:35][N:10]2[C:11]3[C:16]([C:17]([C:18]4[C:19](=[O:34])[NH:46][C:21](=[O:20])[C:22]=4[C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]([CH3:32])[CH:24]=4)=[C:9]2[CH2:8]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:41])=[O:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81560Methanesulfonic anhydride2×HCID 10412974HCID 10412974, compound

Product 1

HCID 19696325HCID 19696325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg of the pyrroledione product of Example 13 in 50 ml of dichloromethane was treated with 218 mg of methanesulfonic anhydride and 1 ml of pyridine. The resulting solution was stirred at room temperature under a nitrogen atmosphere for 1 hour. An additional 20 mg of methanesulfonic anhydride were then added and stirring was continued for 0.5 hour. The mixture was washed with water, dried and evaporated. Crystallization of the residue from ethyl acetate/petroleum ether gave 540 mg of 3-[6,7,8,9-tetrahydro-8-(2-methylsulfonyloxyethyl)pyrido-[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 244°-245° C.

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 hour
  3. washThe mixture was washed with water
  4. customdried
  5. customevaporated
  6. customCrystallization of the residue from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-62ed5dcdebf74a80970d7a63f66f7e8d
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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