Potassium Iodide → HCID 66797424, compound

HRID 1020752Notes

Reaction equation

HRID 1020752 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]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[CH:16]=1)[CH3:14])[CH:6]=[N:5]2.[C:28]([N:35]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[N:36]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>O1CCOCC1.C(OCC)(=O)C>[C:31]([O:30][C:28]([N:35]1[CH:39]=[C:38]([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]([N:21]4[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]4)[CH:16]=2)[CH3:14])[CH:6]=[N:5]3)[CH:37]=[N:36]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 66797363HCID 66797363, compound

Product 1

HCID 66797424HCID 66797424, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of (6-Bromo-quinoxalin-2-yl)-{(R)-1-[3-(4-methyl-piperazin-1-yl)-phenyl]ethyl}-amine (0.250 g, 1 eq., 0.588 mmol), 1-Boc-4-pyrazole boronic acid pinacol ester (0.190 g, 1.1 eq., 0.647 mmol), caesium carbonate (0.764 g, 4.0 eq., 2.35 mmol) and potassium iodide (0.010 g, 0.1 eq., 0.00588 mmol) in 1,4-dioxane (15 mL) 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)) (0.015 g, 0.05 eq., 0.029 mmol) was added at room temperature. The reaction mixture was heated at 105° C. in a microwave reactor for 180 minutes. After completion of the reaction (confirmed by TLC), the organic mixture was diluted with ethyl acetate (325 mL) and washed with water (100 mL×3) and brine (100 mL). The organic layer was dried and concentrated under vacuum to give a crude residue.

Workup

  1. customwas degassed at RT under vacuum
  2. additionFu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.015 g, 0.05 eq., 0.029 mmol) was added at room temperature
  3. customAfter completion of the reaction (confirmed by TLC)
  4. washwashed with water (100 mL×3) and brine (100 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ebfff6470d4f462cbe6e3f65be972a28
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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