Water → (S)-methyl 2-(1H-indazol-5-yl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylate

HRID 1403536

Reaktionsgleichung

Reaktionsgleichung von HRID 1403536
[CH3:1][N:2]([C@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])[C:3]1[C:4](OS(C(F)(F)F)(=O)=O)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=2.CC1(C)C(C)(C)OB([C:41]2[CH:42]=[C:43]3[C:47](=[CH:48][CH:49]=2)[N:46](C(OC(C)(C)C)=O)[N:45]=[CH:44]3)O1.C([O-])([O-])=O.[K+].[K+].O>COCCOC.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>[NH:46]1[C:47]2[C:43](=[CH:42][C:41]([C:4]3[C:3]([N:2]([CH3:1])[C@H:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:26])=[N:12][C:11]4[C:6](=[CH:7][CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=4)[N:5]=3)=[CH:49][CH:48]=2)[CH:44]=[N:45]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18525862tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylateHCID 86670575(S)-methyl 3-(methyl(1-phenylethyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Produkt 1

HCID 70664959(S)-methyl 2-(1H-indazol-5-yl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylateAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (432 mg, crude) in ethylene glycol dimethyl ether (5 mL) was added tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (201 mg, 0.58 mmol), K2CO3 (55 mg, 0.40 mmol), Pd(PPh3)4 (392 mg, 0.34 mmol) and water (1.5 mL) with stirring overnight at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum, dissolved in water (100 mL), extracted with ethyl acetate (3×30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (10% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(1H-indazol-5-yl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylate as a yellow solid (144 mg).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutiondissolved in water (100 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customwas purified via silica gel chromatography (10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-f6d4aefb1f484d49a9f436dea3da3f3b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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