Thionyl Chloride → HCID 67147535, compound

HRID 490527Notes

Reaction equation

HRID 490527 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]([CH3:18])[CH:11]=[C:10]2[C:19]1[N:29]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:22]2=[N:23][CH:24]=[CH:25][C:26]([CH2:27]O)=[C:21]2[CH:20]=1.C(=O)([O-])O.[Na+]>CN(C=O)C.ClCCl>[Cl:3][CH2:27][C:26]1[CH:25]=[CH:24][N:23]=[C:22]2[N:29]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:19]([C:10]3[C:9]4[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:7]([O:6][CH3:5])[CH:8]=4)[N:12]([CH3:18])[CH:11]=3)=[CH:20][C:21]=12

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 67147944HCID 67147944, compound

Product 1

HCID 67147535HCID 67147535, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.089 cm3 of thionyl chloride and five drops of DMF are added to a solution of 0.4 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 4 cm3 of dichloromethane, at a temperature in the region of 20° C. The reaction medium is stirred at this same temperature for 4 hours. Ice is added and the reaction medium is then neutralized with saturated sodium hydrogen carbonate solution. 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/ethyl acetate 97.5/2.5 by volume as eluent), 0.234 g of 4-chloromethyl-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is obtained, the characteristics of which are as follows:

Workup

  1. additionIce is added
  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/ethyl acetate 97.5/2.5 by volume as eluent)

Sources & evidence

ORD record
ord-cadcf033035f47ad902aff99b23a1021
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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