Pyridine → 3-[6,7,8,9-tetrahydro-8-(methylsulphonyloxymethyl)pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 863671Notes

Reaction equation

HRID 863671 reaction equation
C(O[CH2:5][CH:6]1[CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=O)[O:19][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=O)C.[CH3:36][S:37]([O:40]S(C)(=O)=O)(=[O:39])=[O:38].[N:45]1C=CC=CC=1>ClCCl>[CH3:36][S:37]([O:40][CH2:5][CH:6]1[CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:19])[NH:45][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81560Methanesulfonic anhydride2×HCID 103898823-[8-(Acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione

Product 1

HCID 196963343-[6,7,8,9-tetrahydro-8-(methylsulphonyloxymethyl)pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 170 mg of the pyrroledione product of Example 1 in 55 ml of dichloromethane was treated with 87 mg of methanesulfonic anhydride and 1 ml of pyridine. The resulting solution was stirred under nitrogen for 1 hour. An additional 30 mg of methanesulfonic anhydride were then added. After 1 hour, the mixture was washed with water, dried and evaporated. Crystallization of the residue from ethyl acetate/n-hexane gave 150 mg of 3-[6,7,8,9-tetrahydro-8-(methylsulphonyloxymethyl)pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 259°-261° C.

Workup

  1. waitAfter 1 hour
  2. washthe mixture was washed with water
  3. customdried
  4. customevaporated
  5. customCrystallization of the residue from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-a345cb6c0e434ce4add27715c9f0d56c
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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