Azidotrimethylsilane → HCID 178487664, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial, (E)-3-(4-((2-(4-fluorophenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylamide (41 mg, 0.098 mmol) and Bu2SnO (2.433 mg, 9.77 μmol) were suspended in DME (3 mL). The vial was charged with TMSN3 (0.013 mL, 0.098 mmol) and the reaction was heated for 60 min at 180° C. under microwave radiation. The reaction mixture was filtered to remove solids and concentrated onto silica gel. The crude material was purified by column chromatography (SiO2, 1-20% DCM/MeOH) to afford (E)-5-(4-((2-(4-fluorophenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)styryl)-1H-tetrazole (31 mg, 0.070 mmol, 71.4% yield) as an orange solid. 1H NMR (400 MHz, CD3OD) δ ppm=3.78 (s, 3 H) 6.80-6.91 (m, 3 H) 6.96-7.07 (m, 3 H) 7.19 (d, J=8.59 Hz, 1 H) 7.34 (d, J=2.53 Hz, 1 H) 7.35-7.52 (m, 3 H) 7.58-7.74 (m, 2 H).

Provenance & Evidence