Pyridine → HCID 86612141, compound

HRID 490523Notes

Reaction equation

HRID 490523 reaction equation
N1C=CC=CC=1.CS([O:11][S:12]([CH3:15])(=[O:14])=[O:13])(=O)=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]([CH3:29])[CH:22]=[C:21]2[C:30]1[N:40]([S:41]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)(=[O:43])=[O:42])[C:33]2=[N:34][CH:35]=[CH:36][C:37]([CH2:38]O)=[C:32]2[CH:31]=1>ClCCl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]([CH3:29])[CH:22]=[C:21]2[C:30]1[N:40]([S:41]([C:44]2[CH:45]=[CH:46][C:47]([CH3:50])=[CH:48][CH:49]=2)(=[O:43])=[O:42])[C:33]2=[N:34][CH:35]=[CH:36][C:37]([CH2:38][O:11][S:12]([CH3:15])(=[O:13])=[O:14])=[C:32]2[CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81560Methanesulfonic anhydrideHCID 67147944HCID 67147944, compound

Product 1

HCID 86612141HCID 86612141, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.064 g of pyridine and 0.092 g of methanesulfonic anhydride are added to a solution of 0.13 g of [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-yl]methanol in 5 cm3 of dichloromethane, at a temperature in the region of −10° C. The reaction medium is stirred at this same temperature for one hour, and then at room temperature for 24 hours. Ice and 15 cm3 of dichloromethane are added. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluent), 0.044 g of methanesulfonic acid 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl ester is obtained, the characteristics of which are as follows:

Workup

  1. waitat room temperature for 24 hours
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluent)

Sources & evidence

ORD record
ord-1e64875eb187463f96f85941c348dccd
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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