Potassium Iodide → HCID 66797397, compound

HRID 1020730Notes

Reaction equation

[CH2:1]([N:8]([CH3:20])[C:9]1[CH:18]=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](Cl)[CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>O1CCOCC1>[C:24]([O:23][C:21]([N:28]1[CH:32]=[C:31]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]=[C:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:20])[CH:18]=[N:17]3)[CH:30]=[N:29]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

N-benzyl-6-chloro-N-methylquinoxalin-2-amine (0.250 g, 0.88 mmol), N-Boc-4-pyrazole boronic acid pinacol ester (0.310 g, 1.05 mmol), caesium carbonate (1.14 g, 3.52 mmol), potassium iodide (0.014 g, 0.088 mmol) were added to 1,4-dioxane (12 mL) at RT. The mixture was degassed under vacuum and was placed under an atmosphere of nitrogen (the process was repeated twice). Fu's catalyst (Bis(tri-tert-butylphosphine) palladium(0)) (0.022 g, 0.04 mmol) was added at RT. The reaction mixture was heated at 100° C. by irradiation for 180 min in a microwave reactor. The organic mixture was diluted with ethyl acetate (150 mL) and washed with water (20 mL×3) followed by brine (20 mL). The organic solvent was distilled under vacuum to afford crude compound.

Workup

customThe mixture was degassed under vacuum
additionFu's catalyst (Bis(tri-tert-butylphosphine) palladium(0)) (0.022 g, 0.04 mmol) was added at RT
additionThe organic mixture was diluted with ethyl acetate (150 mL)
washwashed with water (20 mL×3)
distillationThe organic solvent was distilled under vacuum
customto afford crude compound

Sources & evidence

ORD record: ord-d246231dd1d14cbbbd89667b1e2bc413
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716473B2

Reaction notes

Loading…