Acetonitrile → 1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-3-(3-pyridinyl)-

HRID 879472Notes

Reaction equation

HRID 879472 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C(#N)C.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 867002871H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-3-(3-pyridinyl)-

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a screw top reaction tube was placed 5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (1.2 g, 2.52 mmol, prepared according to WO2011/149950), pyridin-3-ylboronic acid (371 mg, 3.02 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (177 mg, 0.25 mmol). Degassed acetonitrile (16 mL) and 1 N Na2CO3 (16 mL) was added and the reaction tube was purged with argon, sealed and heated at 60° C. for 2 h. The reaction was cooled, filtered through a Celite pad and concentrated under reduced pressure. The residue was partitioned between EtOAc/water and extracted. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a solid. Trituration of the solid with hexanes and dichloromethane gave the desired compound. LCMS-ESI+: calc'd for C19H14BrN3O2S: 428.0 (M+H+); found: 428.2 (M+H+).

Workup

  1. customTo a screw top reaction tube was placed
  2. customthe reaction tube was purged with argon
  3. customsealed
  4. temperatureThe reaction was cooled
  5. filtrationfiltered through a Celite pad
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was partitioned between EtOAc/water
  8. extractionextracted
  9. washThe organic layer was washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customto give a solid

Sources & evidence

ORD record
ord-03f0b00115c249249941851b558affdb
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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