Potassium Iodide → HCID 49821034, compound

HRID 1020738Notes

Reaction equation

HRID 1020738 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH3:13])[CH:6]=[N:5]2.C([N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1)(OC(C)(C)C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>O1CCOCC1.C(OCC)(=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:12]([CH3:13])[C:7]2[CH:6]=[N:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:32]4[CH:33]=[N:29][NH:30][CH:31]=4)[CH:3]=3)[N:8]=2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 66797584HCID 66797584, compound

Product 1

HCID 49821034HCID 49821034, compound

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

(6-Bromo-quinoxalin-2-yl)-(4-fluoro-benzyl)-methyl-amine (0.4 g, 1.1 mmol), 1-Boc-4-pyrazole boronic acid pinacol ester (0.4 g, 1.3 mmol), caesium carbonate (1.5 g, 4.6 mmol) and potassium iodide (0.018 g, 0.1 mmol) were dissolved in 1,4-dioxane (20 mL) at room temperature. The reaction mixture was degassed at RT under vacuum and placed under an atmosphere of nitrogen. The process was repeated twice and slowly Bis(tri-tert-butylphosphine)palladium(0) (0.059 g 0.1 mmol) was added at room temperature. The reaction mixture was heated by microwave irradiation at 110° C. for 180 min. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 mL) and washed with water (3×20 mL) and brine (20 mL). The organic volatiles were removed under vacuum to give a residual solid.

Workup

  1. customThe reaction mixture was degassed at RT under vacuum
  2. customAfter completion of the reaction
  3. washwashed with water (3×20 mL) and brine (20 mL)
  4. customThe organic volatiles were removed under vacuum
  5. customto give a residual solid

Sources & evidence

ORD record
ord-778ca748cc19423b945a833afa8ee096
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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