Cesium carbonate → 1H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-

HRID 887369Notes

Reaction equation

HRID 887369 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[B-](F)(F)(F)[CH3:22].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:22][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-HCID 23692566Potassium Trifluoro(methyl)borate

Product 1

HCID 497589241H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-Yield 47%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (5 g, 14.29 mmol), potassium trifluoro(methyl)borate (2.62 g, 21.43 mmol), cesium carbonate (12.56 g, 38.57 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.16 g, 1.43 mmol) in THF (150 mL) and water (15 mL) was heated at reflux for 18 hours. The reaction mixture was cooled down to ambient and partitioned between EtOAc (100 mL) and water (100 mL). The organic phase was separated, washed with 1N HCl (100 mL) and brine (100 mL), then, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to give the title compound as a white solid (1.903 g, 47% yield).

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled down to ambient and
  3. custompartitioned between EtOAc (100 mL) and water (100 mL)
  4. customThe organic phase was separated
  5. washwashed with 1N HCl (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-ddbf5297d491402795fb18ed8450f792
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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