1-Methyl-5-(tributylstannyl)-1H-pyrazole → HCID 59164478, Verbindung

HRID 906594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906594
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](I)[C:7]([CH:11]([F:13])[F:12])=[CH:6][C:5]=1[NH2:14].[CH3:16][N:17]1[C:21]([Sn](CCCC)(CCCC)CCCC)=[CH:20][CH:19]=[N:18]1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:21]2[N:17]([CH3:16])[N:18]=[CH:19][CH:20]=2)[C:7]([CH:11]([F:13])[F:12])=[CH:6][C:5]=1[NH2:14]

Komponenten

5

Edukt 2

HCID 218674551-Methyl-5-(tributylstannyl)-1H-pyrazoleHCID 591644452-Amino-4-difluoromethyl-5-iodo-benzoic acid methyl ester

Produkt 1

HCID 59164478HCID 59164478, VerbindungAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-amino-4-difluoromethyl-5-iodo-benzoic acid methyl ester (750 mg, 2.29 mmol) in dioxane (30 mL) were added 1-methyl-5-tributylstannanyl-1H-pyrazole (1.28 g, 1.5 equiv) and Pd(PPh3)2Cl2 (246 mg, 0.15 equiv) and the resulting mixture was stirred at 90° C. for 18 h. The solvent was removed in vacuo to afford a dark oil. The crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 50:50)) to provide the title compound as a yellow oil (200 mg, 31%). ES-MS: m/z 282.3 [M+H]+, rt 4.97 min.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customto afford a dark oil
  3. customThe crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 50:50))

Quellen und Nachweise

ORD-Eintrag
ord-c2028ae3ddd443919a0cde5eb216726d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012988B2

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