Sodium Carbonate → methyl 3-(benzyl(methyl)amino)-2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)quinoxaline-6-carboxylate

HRID 1403532

반응식

HRID 1403532 반응식
[CH2:1]([N:8]([CH3:31])[C:9]1[C:10](OS(C(F)(F)F)(=O)=O)=[N:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[C:42]3[C:46](=[CH:47][CH:48]=2)[N:45]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[N:44]=[CH:43]3)O1.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH2:1]([N:8]([CH3:31])[C:9]1[C:10]([C:40]2[CH:41]=[C:42]3[C:46](=[CH:47][CH:48]=2)[N:45]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[N:44]=[CH:43]3)=[N:11][C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 18525862tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylateHCID 86670574Methyl 3-(benzyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

생성물 1

HCID 70665130methyl 3-(benzyl(methyl)amino)-2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)quinoxaline-6-carboxylate수율 43.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

To a solution of methyl 3-(benzyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (300 mg, crude) in ethylene glycol dimethyl ether (7 mL) was added tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (181 mg, 0.53 mmol), sodium carbonate (93 mg, 0.88 mmol), and Pd(PPh3)4 (25 mg, 0.02 mmol). The resulting solution was stirred for 1 h at 90° C. under an inert atmosphere of nitrogen, quenched with water (100 mL) and extracted with dichloromethane (3×50 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (3% ethyl acetate in petroleum ether) to afford methyl 3-(benzyl(methyl)amino)-2-(1-(tert-butoxycarbonyl)-1H-indazol-5-yl)quinoxaline-6-carboxylate as a yellow solid (120 mg).

후처리

  1. customquenched with water (100 mL)
  2. extractionextracted with dichloromethane (3×50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified via silica gel chromatography (3% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-6acf9331ce644a9ea0aebaba1f32169a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912188B2

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