Sodium Carbonate → 3-(2,6-difluoropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 68342Notes

Reaction equation

HRID 68342 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12](B3OC(C)(C)C(C)(C)O3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:28][C:29]1[CH:34]=[C:33](I)[CH:32]=[C:31]([F:36])[N:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.O>[F:28][C:29]1[CH:34]=[C:33]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH:11]=2)[CH:32]=[C:31]([F:36])[N:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 217473652,6-Difluoro-4-iodopyridineHCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Product 1

HCID 674403733-(2,6-difluoropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (7.26 g, 18.9 mmol), 2,6-difluoro-4-iodopyridine (4.14 g, 17.2 mmol, Eur. J. Org. Chem., 2004, 1018 and Org. Lett. 2007, 5175), dichlorobis(triphenylphosphine) palladium(II) (0.482 g, 0.687 mmol) and 1M aqueous sodium carbonate (13.7 mL, 13.7 mmol) in dimethoxyethane/ethanol/water (7:2:3) (80 mL) was degassed and heated at 80° C. for 1.5 hours. After cooling, the suspension was filtered, washed with water and ether, and concentrated to give the crude title compound. The filtrate was diluted with water and extracted twice with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and purified using an ISCO Companion flash system eluting with dichloromethane/hexane (7:3 to 9:1) to give the title compound. The combined products were used in the next step without further purification.

Workup

  1. customwas degassed
  2. temperatureAfter cooling
  3. filtrationthe suspension was filtered
  4. washwashed with water and ether
  5. concentrationconcentrated
  6. customto give the crude title compound
  7. extractionextracted twice with dichloromethane
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified
  12. washeluting with dichloromethane/hexane (7:3 to 9:1)

Sources & evidence

ORD record
ord-80918da8537a479b9642295842d347d7
Source dataset
uspto-grants-2014_09
Patent number
US08822446B2

Reaction notes

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