N-Methyl dicyclohexylamine → 5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde

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Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=[O:12])[CH:10]=1)[NH:7][N:6]=[CH:5]2.CN(C1CCCCC1)C1CCCCC1.Cl[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:7]=2)[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

5-Chloro-1H-indazole-7-carbaldehyde (5.6 g, 31.0 mmol) and N-methyldicyclohexylamine (9 mL, 41.9 mmol) were suspended in tetrahydrofuran (100 mL), cooled to 0° C., and treated with (2-(chloromethoxy)ethyl)trimethylsilane (8.3 mL, 46.5 mmol). Cooling was removed and stirring continued for 4 h. The reaction was poured into ethyl acetate, washed with water (3×), 1 M potassium bisulfate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (25% ethyl acetate/hexanes) gave 5.6 g (58%) as a faint yellow oil. 1H-NMR (CDCl3, 300 MHz) δ 10.50 (s, 1H), 8.21 (s, 1H), 7.94 (d, J=2.2 Hz, 1H), 7.82 (d, J=1.8 Hz, 1H), 5.78 (s, 2H), 3.62-3.67 (m, 2H), 0.90-0.96 (m, 2H), 0.05 (s, 9H). Mass spec.: 332.98 (MNa)+.

Aufarbeitung

temperatureCooling
customwas removed
additionThe reaction was poured into ethyl acetate
washwashed with water (3×), 1 M potassium bisulfate (2×), brine (2×)
dry with materialdried over sodium sulfate
concentrationconcentrated
customColumn chromatography on silica gel (25% ethyl acetate/hexanes) gave 5.6 g (58%) as a faint yellow oil

Quellen und Nachweise

ORD-Eintrag: ord-80797878675a44938c5df1172f4a4094
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08026257B2

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