Potassium Phosphate, Tribasic → HCID 70665079, compound

HRID 1403480Notes

Reaction equation

HRID 1403480 reaction equation
Cl[C:2]1[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[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.CC1(C)C(C)(C)OB([C:29]2[O:30][CH:31]=[CH:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)O1.[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>[CH3:16][N:12]([CH:13]([CH3:15])[CH3:14])[C:11]1[C:2]([C:29]2[O:30][CH:31]=[CH:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:17]([O:19][CH3:20])=[O:18])=[CH:6][CH:5]=2

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 70657354HCID 70657354, compoundHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70665079HCID 70665079, compoundYield 73%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
95 °C

Procedure

To a solution of methyl 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (140 mg, 0.48 mmol) in dioxane (5.0 mL) and water (3 drops) was added 4,4,5,5-tetramethyl-2-(3-phenylfuran-2-yl)-1,3,2-dioxaborolane (270 mg, 1.00 mmol), K3PO4 (211 mg, 0.99 mmol) and Pd(PPh3)4 (28 mg, 0.02 mmol) with stirring for 1 h at 95° C. in an oil bath maintained under an inert atmosphere of nitrogen. The reaction mixture was concentrated under vacuum to give a residue, which was purified by silica gel chromatography (2% ethyl acetate in petroleum ether) to afford methyl 3-[methyl(propan-2-yl)amino]-2-(3-phenylfuran-2-yl)quinoxaline-6-carboxylate as a light yellow solid (140.0 mg, 73%).

Workup

  1. temperaturemaintained under an inert atmosphere of nitrogen
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customto give a residue, which
  4. customwas purified by silica gel chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3f85230bd1cc463999b235486dd53da8
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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