Dichloromethane → HCID 24949073, compound

Participants

Reaction Steps

A sample of 14b (3.0 mg, 0.009 mmol) was dissolved in a mixture of MeOH (0.1 mL): CH2Cl2 (0.1 mL). TMSCHN2 (7 μL, 0.013 mmol) was added dropwise causing gas to evolve, and after 0.5 h the reaction mixture was quenched with the dropwise addition of AcOH (50 μL). All volatiles were removed under reduced pressure to afford a residue that was purified by preparative thin layer chromatography (SiO2, 50% EtOAc-hexanes). The title compound (0.735 mg, 23%) was isolated along with the two other regioisomers (16; 1.01 mg, 32%; 17; 0.496 mg, 16%) as a colorless solid: 1H NMR (CDCl3, 500 MHz) δ 8.71 (dd, 1H, J=0.9, 4.9 Hz), 8.33 (d, 1H, J=8.0 Hz), 7.88 (dt, 1H, J=1.8, 7.8 Hz), 7.41 (ddd, 1H, J=1.1, 4.9, 7.6 Hz), 7.28 (m, 2H), 7.16 (m, 3H), 4.37 (s, 3H), 3.28 (t, 2H, J=7.4 Hz), 2.61 (t, 2H, J=7.7 Hz), 1.78 (m, 2H), 1.64 (m, 2H), 1.42 (m, 4H); HRMS-ESI-TOF m/z 349.2020 ([M+H]+, C21H24N4O requires 349.2023). Tetrazoles (15a-15e, 19a, 19b):

Provenance & Evidence