Sodium Carbonate → (S)-methyl 2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate

HRID 1403513

Reaktionsgleichung

Reaktionsgleichung von HRID 1403513
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:4][N:3]1[C:14]1[C:15](OS(C(F)(F)F)(=O)=O)=[N:16][C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)OB([C:48]2[CH:49]=[C:50]3[C:54](=[CH:55][CH:56]=2)[N:53]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[N:52]=[CH:51]3)OC1(C)C>COCCOC.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>[C:60]([O:59][C:57]([N:53]1[C:54]2[C:50](=[CH:49][C:48]([C:15]3[C:14]([N:3]4[CH2:4][CH2:5][N:6]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=5)[CH2:7][C@@H:2]4[CH3:1])=[N:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=4)[N:16]=3)=[CH:56][CH:55]=2)[CH:51]=[N:52]1)=[O:58])([CH3:63])([CH3:61])[CH3:62]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 18525862tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylateHCID 86670573(S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Produkt 1

HCID 70665358(S)-methyl 2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylateAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (240 mg, 0.38 mmol) in ethylene glycol dimethyl ether (20 ml) was added Pd(PPh3)4 (27 mg, 0.02 mmol), sodium carbonate (74.3 mg, 0.69 mmol) in water (6 ml), and tert-butyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (300 mg, 0.87 mmol). After stirring 90 minutes at 90° C. in an oil bath, the reaction was then quenched by the addition of water (200 ml), extracted with dichloromethane (3×30 ml), dried over anhydrous magnesium sulfate and concentrated under vacuum to afford a residue, which was purified via silica gel chromatography (20% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate as a yellow solid (134 mg, 60%).

Aufarbeitung

  1. customthe reaction was then quenched by the addition of water (200 ml)
  2. extractionextracted with dichloromethane (3×30 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto afford a residue, which
  6. customwas purified via silica gel chromatography (20% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-049a0f96a5c44bcc8258a86593979ea9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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