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

反応式

HRID 1403513 の反応式
[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]

参加物

7

反応物 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

生成物 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-carboxylate収率 60.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-049a0f96a5c44bcc8258a86593979ea9
出典データセット
uspto-grants-2014_12
特許番号
US08912188B2

関連ノート

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