Water → methyl 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate

HRID 1403493Notes

Reaction equation

HRID 1403493 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.[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)[NH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].O>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>[CH:14]([N:12]([CH3:13])[C:11]1[C:2]([C:28]2[CH:29]=[C:30]3[C:25](=[CH:26][CH:27]=2)[NH:24][CH:23]=[C:22]3[CH3:21])=[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)([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 210726073-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70664626methyl 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylateYield 45%

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 (150 mg, 0.51 mmol) in dioxane (5 mL) was added 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (395 mg, 1.54 mmol), K2CO3 (106 g, 0.77 mmol), Pd(PPh3)4 (30 mg, 0.03 mmol) and water (5 drops). The resulting solution was stirred for 5 h at 90° C., and then poured into water (100 mL), extracted with DCM (4×50 mL), dried over anhydrous sodium sulfate and then concentrated under vacuum to give a residue. The residue was purified via silica gel chromatography (25% ethyl acetate in petroleum ether) to afford methyl 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate as a yellow solid (80 mg, 45%).

Workup

  1. extractionextracted with DCM (4×50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue
  5. customThe residue was purified via silica gel chromatography (25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e927f4ad0232479585973f20b3bb0bb4
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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