Trimethylsilyl iodide → 4-[2-(4-Fluorophenyl)-7-piperidin-4-ylimidazo-[1,2-a]pyridin-3-yl]piperidin-2-ylamine
Reaktionsgleichung
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([CH:17]4[CH2:22][CH2:21][N:20](C(OCC5C=CC=CC=5)=O)[CH2:19][CH2:18]4)=[CH:16][C:11]3=[N:10][C:9]=2[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH:5]=[CH:4][N:3]=1.[Si](I)(C)(C)C>CC#N>[F:39][C:36]1[CH:35]=[CH:34][C:33]([C:9]2[N:10]=[C:11]3[CH:16]=[C:15]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[CH:14]=[CH:13][N:12]3[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:38][CH:37]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Benzyl carbonate 37 (190 mg, 0.36 mmol) was slurried in CH3CN (5 mL) in a 28 mL Pyrex Plus tube. TMSI (720 mg, 3.6 mmol) was then added, and the reaction was allowed to stir at room temperature for 2 hours. The reaction was then concentrated under reduced pressure. The crude product was then dissolved in 10 mL CH2Cl2, plus a few drops of methanol, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 38: 140 mg (100%). 1H NMR (400 MHz, CDCl3) δ 1.67 (m, 2H), 1.84 (m, 2H), 2.67 (m, 1H), 2.74 (m, 2H), 3.18 (m, 2H), 5.03 (s, 2H), 6.44 (d, J=5.2 Hz, 1H), 6.77 (d, J=7.2 Hz, 1H), 7.05 (t, J=8.8 Hz, 2H), 7.43 (bs, 1H), 7.56 (m, 2H), 8.04 (d, J=5.2 Hz, 1H), 9.36 (d, J=7.2 Hz, 1H). MS (ESI+) 389.2.