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Lithium hexamethyldisilazane → 7-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79441
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 79441
[CH2:1]([C:3]1[C:11]2[C:10]([NH2:12])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]([CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[N:15]=2)[N:4]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:31][C:32]1[CH:37]=[CH:36][N:35]2[C:38]([C:41](OC)=[O:42])=[CH:39][N:40]=[C:34]2[CH:33]=1>C1COCC1.CO.C(Cl)Cl>[Br:31][C:32]1[CH:37]=[CH:36][N:35]2[C:38]([C:41]([NH:12][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]4[C:11]=3[C:3]([CH2:1][CH3:2])=[N:4][N:5]4[CH2:13][C:14]3[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[N:15]=3)=[O:42])=[CH:39][N:40]=[C:34]2[CH:33]=1
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Komponenten

6

Edukt 3

HCID 2733832Lithium hexamethyldisilazaneHCID 67259752Methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylateHCID 672598083-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

Produkt 1

HCID 672612817-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution 3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (328 mg, 1.22 mmol) in anhydrous THF (3 mL) was added under a nitrogen atmosphere at ambient temperature lithium bis(trimethylsilyl)amide (1.0 M in THF, 1.15 mL). The resulting mixture was stirred at ambient temperature for 10 minutes, then added dropwise to a chilled (ice-water bath) solution of methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (140 mg, 0.55 mmol) in anhydrous THF (3 mL). The cold bath was removed, and the reaction mixture was allowed to warm to ambient temperature, and quenched with water. The resulting suspension was extracted thoroughly with DCM, the combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with 5% MeOH-DCM as eluent to afford 219 mg of desired product as a yellow solid.

Aufarbeitung

  1. additionadded dropwise to
  2. customThe cold bath was removed
  3. temperatureto warm to ambient temperature
  4. customquenched with water
  5. extractionThe resulting suspension was extracted thoroughly with DCM
  6. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto afford the crude product

Quellen und Nachweise

ORD-Eintrag
ord-f75a56197e3d4287b252b3ec5dd6f04d
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08841455B2

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