3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde → (E)-3-(2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

The title compound was synthesized according to the method of Example A15A, utilizing 1-methyl-4-(5-vinylpyridin-2-yl)piperazine (65 mg, 0.32 mmol) and 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (100 mg, 0.25 mmol), with heating in a sealed tube at 90° C. overnight instead of with microwave irradiation. Purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound to as a pale orange material (46 mg, 39%). 1H NMR (400 MHz, CD3OD) δ ppm 10.14 (s, 1 H), 8.34 (d, J=2.26 Hz, 1.0 H), 8.24-8.28 (m, 2 H), 8.00 (dd, J=8.91, 2.38 Hz, 1 H), 7.80 (d, J=8.78 Hz, 1 H), 7.51 (d, J=16.56 Hz, 1 H), 7.36 (d, J=16.56 Hz, 1 H), 6.97 (d, J=9.29 Hz, 1 H), 5.85 (s, 2 H), 3.77-3.87 (m, 4 H), 3.63 (t, J=7.91 Hz, 2 H), 3.06-3.15 (m, 4 H), 2.75 (s, 3 H), 0.88 (t, J=8.03 Hz, 2 H), −0.09 (s, 9 H); MS ESI 478.3 [M+H]+, calcd for [C26H35N5O2Si+H]+ 478.7.

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