Dimethylformamide → HCID 68467994, compound

HRID 506819Notes

Reaction equation

HRID 506819 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21]O)=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:34][CH3:35].S(Cl)([Cl:38])=O.CN(C=O)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:38][CH2:21][C:20]1[CH:19]=[CH:18][N:17]=[C:16]2[N:23]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:13]([C:9]3[C:7]4=[N:8][C:3]([O:2][CH3:1])=[C:4]([O:34][CH3:35])[CH:5]=[C:6]4[N:11]([CH3:12])[CH:10]=3)=[CH:14][C:15]=12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68470494HCID 68470494, compound

Product 1

HCID 68467994HCID 68467994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.2 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methanol in 50 cm3 of dichloromethane, at a temperature in the region of 20° C., are added 0.747 cm3 of thionyl chloride and 0.3 cm3 of DMF. The reaction medium is stirred at this same temperature for 2 hours. Ice is added and the reaction medium is then neutralized with saturated sodium hydrogencarbonate 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 95/05 by volume as eluents), 2.64 g of 3-[4-chloromethyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridine are obtained with the following characteristics:

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 95/05 by volume as eluents), 2.64 g of 3-[4-chloromethyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridine
  7. customare obtained with the following characteristics

Sources & evidence

ORD record
ord-23c9a363a8fe43449f38726d09ea5f86
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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