Potassium Iodide → HCID 66797422, compound

HRID 1020754Notes

Reaction equation

HRID 1020754 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[CH3:14])[CH:6]=[N:5]2.[C:23]([N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>O1CCOCC1>[C:26]([O:25][C:23]([N:30]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([NH:12][C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH3:14])[CH:6]=[N:5]3)[CH:32]=[N:31]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 66797578HCID 66797578, compound

Product 1

HCID 66797422HCID 66797422, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

(6-Bromo-quinoxalin-2-yl)-[(R)-1-(3-methoxy-phenyl)-ethyl]-amine (0.3 g, 0.83 mmol), N-Boc-4-pyrazole boronic acid pinacol ester (0.27 g, 0.92 mmol), caesium carbonate (1.08 g, 3.34 mmol) and potassium iodide (0.014 g, 0.083) were dissolved in 1,4-dioxane (15 mL). The reaction mixture was degassed at RT under vacuum and placed under an atmosphere of nitrogen. The process was repeated twice and Fu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.021 g, 0.041 mmol) was added at RT. The reaction mixture was heated at 110° C. in a microwave reactor for 180 minutes. The organic mixture was diluted with ethyl acetate (150 mL), washed with water (15 mL×2) and brine (15 mL) and was then dried over Na2SO4. The organic volatiles were evaporated in vacuo to afford crude product.

Workup

  1. customThe reaction mixture was degassed at RT under vacuum
  2. additionFu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.021 g, 0.041 mmol) was added at RT
  3. additionThe organic mixture was diluted with ethyl acetate (150 mL)
  4. washwashed with water (15 mL×2) and brine (15 mL)
  5. dry with materialwas then dried over Na2SO4
  6. customThe organic volatiles were evaporated in vacuo
  7. customto afford crude product

Sources & evidence

ORD record
ord-0d2c75215d2846689bf5a96ef0461756
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

Loading…