Cesium carbonate → HCID 68498722, compound

HRID 1710702Notes

Reaction equation

HRID 1710702 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:14])=[N:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[C:2]1[N:3]=[CH:4][C:5]([NH2:14])=[N:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 447551543-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59457578HCID 59457578, compound

Product 1

HCID 68498722HCID 68498722, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

An oven dried resealable Schlenk tube was charged with 5-bromo-6-pyridin-3-ylpyrazin-2-amine (Preparation 6, 0.3 g, 1.17 mmol), 3-cloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.56 g, 2.35 mmol), cesium carbonate (1.15 g, 3.525 mmol) in dioxane (10 mL) and water (2.8 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (58 mg, 0.071 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 90° C. oil bath. After 16 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (95:5 dichloromethane/methanol) gave the title compound (0.16 g, 48%) as a solid.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 90° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase extracted twice with ethyl acetate
  8. washthe organic layers washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-641fb299a3ea4f2ba4efb70c97811f2a
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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