Potassium Phosphate, Tribasic → HCID 70665012, compound

HRID 1403317Notes

Reaction equation

HRID 1403317 reaction equation
Cl[C:2]1[C:11]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=2)[N:3]=1.[F:21][C:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][N:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:21][C:22]1[CH:27]=[C:26]([C:2]2[C:11]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=3)[N:3]=2)[CH:25]=[CH:24][N:23]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27833962-Fluoropyridine-4-boronic acidHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70665012HCID 70665012, compoundYield 69.2%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (300.0 mg, 1.02 mmol) in dioxane (5 mL) was added 2-fluoropyridin-4-ylboronic acid (289.0 mg, 2.06 mmol), K3PO4 (435.0 mg, 2.05 mmol), Pd(PPh3)4 (60 mg, 0.05 mmol) and three drops water under an inert atmosphere of nitrogen. The resulting solution was stirred for 1 h at 90° C. and then quenched by the addition of water (50 mL). The resulting solution was extracted with dichloromethane (5×20 mL) and the organic layers combined, dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether to afford methyl 2-(2-fluoropyridin-4-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid (250 mg, 69%).

Workup

  1. customquenched by the addition of water (50 mL)
  2. extractionThe resulting solution was extracted with dichloromethane (5×20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-189e53c7eea242688dabe9333b7a6eed
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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