Potassium Iodide → HCID 66797545, compound

HRID 1020727Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of benzyl-(6-chloro-quinoxalin-2-yl)-amine (0.250 g, 0.92 mmol, 1 eq), N-Boc-4-pyrazole boronic acid pinacol ester (0.328 g, 1.1 mmol, 1.2 eq), caesium carbonate (1.2 g, 3.71 mmol, 4.03 eq), potassium iodide (0.015 g, 0.09 mmol, 0.1 eq) in 1,4-dioxane (12 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)) (0.023 g, 0.046 mmol) was added at RT. The reaction mixture was heated to 100° C. by microwave irradiation for 180 min. The organic mixture was diluted with ethyl acetate (150) and washed with water (20 mL×2) and brine (20 mL). The organic solvent was evaporated under vacuum to give crude product.

Workup

customwas degassed at RT under vacuum
additionFu's catalyst (bis(tri-tert-butylphosphine)-palladium(0)) (0.023 g, 0.046 mmol) was added at RT
additionThe organic mixture was diluted with ethyl acetate (150)
washwashed with water (20 mL×2) and brine (20 mL)
customThe organic solvent was evaporated under vacuum
customto give crude product

Sources & evidence

ORD record: ord-81e27babcb044450b4a1c7d2126b153f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716473B2

Reaction notes

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