Phenol → HCID 68469165, compound

HRID 506834Notes

Reaction equation

HRID 506834 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[N:9]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:10]([C:12]3[C:16]4=[N:17][C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=[C:15]4[N:14]([CH3:25])[CH:13]=3)=[CH:11][C:4]=12.[C:36]1([OH:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.ClCCl>[CH3:24][O:23][C:18]1[N:17]=[C:16]2[C:12]([C:10]3[N:9]([S:26]([C:29]4[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=4)(=[O:27])=[O:28])[C:5]4=[N:6][CH:7]=[CH:8][C:3]([CH2:2][O:42][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[C:4]4[CH:11]=3)=[CH:13][N:14]([CH3:25])[C:15]2=[CH:20][C:19]=1[O:21][CH3:22]

Participants

7

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 68467994HCID 68467994, compound

Product 1

HCID 68469165HCID 68469165, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.3 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 in 30 cm3 of acetonitrile, at a temperature in the region of 20° C., are added 0.066 cm3 of phenol and 0.486 g of potassium carbonate. The reaction medium is heated at 80° C. for 18 hours. After cooling, the reaction medium is filtered through a sinter funnel and the filtrate is concentrated under reduced pressure. The residue obtained is taken up in 5 cm3 of water and 10 cm3 of dichloromethane. 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 column chromatography (SiO2, dichloromethane/ethyl acetate 97.5/2.5 by volume as eluents), 0.140 g of 5,6-dimethoxy-1-methyl-3-[4-phenoxymethyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-pyrrolo[3,2-b]pyridine is obtained with the following characteristics:

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction medium is filtered through a sinter funnel
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customAfter separation of the phases
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customAfter purification by flash column chromatography (SiO2, dichloromethane/ethyl acetate 97.5/2.5 by volume as eluents)

Sources & evidence

ORD record
ord-801d8bcf21c9404c9338a0c6dfcd6780
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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