1-benzyloxy-5-tributylstannanyl-1H-pyrazole → HCID 59164449, Verbindung

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Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](I)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15].[CH2:17]([O:24][N:25]1[C:29]([Sn](CCCC)(CCCC)CCCC)=[CH:28][CH:27]=[N:26]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:29]2[N:25]([O:24][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:26]=[CH:27][CH:28]=2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 2-amino-4-trifluoromethyl-5-iodo-benzoic acid methyl ester (750 mg, 2.17 mmol) in dioxane (15 mL) were added 1-benzyloxy-5-tributylstannanyl-1H-pyrazole (1.24 g, 2.60 mmol) and Pd(dppf)2Cl2 (177 mg, 0.217 mmol) and the resulting mixture was stirred at 100° C. for 16 h. An additional portion of catalyst (0.1 equiv) was added and the mixture was stirred at 100° C. for an additional 24 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 an off-white solid (263 mg, 31%). ES-MS: m/z 392.3 [M+H]+, rt 6.48 min.

Aufarbeitung

stirringthe mixture was stirred at 100° C. for an additional 24 h
customThe solvent was removed in vacuo
customto afford a dark oil
customThe crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 50:50))

Quellen und Nachweise

ORD-Eintrag: ord-2d8be9d6dbe94465ae0d4fcce0050c6c
Quelldatensatz: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07655666B2

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