Trimethylsilyldiazomethane → HCID 178499415, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 128A (400 mg, 0.856 mmol) in MeOH (3 mL) was added (diazomethyl)trimethylsilane (4.28 ml, 8.56 mmol). The mixture was stirred at 20° C. overnight then concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, gradient 20-100% solvent A in hexane; solvent A=10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (250 mg, 0.519 mmol, 60.7% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.43 (s, 9H) 1.71-1.85 (m, 3H) 1.99-2.12 (m, 1H) 3.66 (s, 3H) 3.70-3.82 (m, 2H) 3.87 (s, 3H) 4.17-4.23 (m, 1H) 4.25-4.33 (m, 3H) 4.52-4.59 (m, 1H) 6.99 (s, 1H) 7.31 (d, J=7.80 Hz, 1H) 7.52 (dd, J=7.97, 1.53 Hz, 1H) 8.40 (d, J=1.70 Hz, 1H); MS (DCI/NH3) m/z 482 (M+H)+.

Provenance & Evidence