Dimethylformamide → HCID 57537482, compound

Participants

Reaction Steps

5-Bromo-4-chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (245 mg, 0.52 mmol) and methoxybenzyl alcohol (723 mg, 5.2 mmol) were dissolved in dimethylformamide (0.25 mL). Sodium hydride (167 mg, 4.2 mmol) was added and the mixture was irradiated in a Personal Chemistry Optimizer at 120° C. for 5 min. The reaction was quenched with water, applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of (ethyl acetate and methanol 9:1) in hexanes to afford 5-Bromo-4-(4-methoxy-benzyloxy)-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (220 mg, 0.38 mmol, 74% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.66 (s, 1H), 7.40 (m, 1H), 7.35 (dd, J=7 Hz, J2=2 Hz, 1H), 7.08 (d, J=8 Hz, 1H), 7.01 (td, J1=7 Hz, J2=1 Hz, 1H), 6.77 (m, 4H), 5.63 (s, 2H), 4.37 (s, 2H), 3.71 (s, 3H), 3.64 (s, 3H), 3.58 (t, J=8 Hz, 1H), 0.83 (t, J=8 Hz, 1H), −0.08 (s, 9H). MS: m/z 569.4/571.3 (M+H+).

Provenance & Evidence