Potassium Iodide → HCID 66797158, compound

HRID 1020756Notes

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]([Cl:21])[CH:16]=1)[CH3:14])[CH:6]=[N:5]2.[C:22]([N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>O1CCOCC1>[C:25]([O:24][C:22]([N:29]1[CH:33]=[C:32]([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]([Cl:21])[CH:16]=2)[CH3:14])[CH:6]=[N:5]3)[CH:31]=[N:30]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (6-Bromo-quinoxalin-2-yl)-[(R)-1-(3-chloro-phenyl)-ethyl]-amine (0.38 g, 1.0 mmol), N-Boc-4-pyrazole boronic acid pinacol ester (0.37 g, 1.2 mmol), caesium carbonate (1.36 g, 4.1 mmol) and potassium iodide (0.017 g, 0.1) in 1,4-dioxane (20 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)) (0.053 g, 0.1 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) and washed with water (20 mL×2) and brine (20 mL). The organic solvent was evaporated in vacuo to afford the crude product.

Workup

customwas degassed at RT under vacuum
additionFu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.053 g, 0.1 mmol) was added at RT
additionThe organic mixture was diluted with ethyl acetate (150 mL)
washwashed with water (20 mL×2) and brine (20 mL)
customThe organic solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-621bdfd024464583a478b8220e0d4b5f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716473B2

Reaction notes

Loading…