Cesium carbonate → HCID 16071665, compound

HRID 1710696Notes

Reaction equation

HRID 1710696 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.CC1(C)C(C)(C)OB([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:7]2[N:6]=[C:5]([NH2:14])[CH:4]=[N:3][C:2]=2[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 59457578HCID 59457578, compound

Product 1

HCID 16071665HCID 16071665, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-6-pyridin-3-ylpyrazin-2-amine (Preparation 6, 0.4 g, 1.59 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.424 g, 2.07 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride dichloromethane complex (1:1) (76 mg, 0.095 mmol) and cesium carbonate (1.55 g, 4.77 mmol) in dioxane (14 mL) and water (3.72 mL) was heated to 150° C. for 10 minutes in the microwave oven. The mixture was partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and evaporated. Silica gel flash chromatography (95:5 dichloromethane/methanol) gave the title compound (0.37 g, 74%) as a solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-961bd91d8f8d4e248bea72075dfc8e37
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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