Triethylamine → 5-(2-Diazo-acetyl)-biphenyl-3-carboxylic acid propylamide

Participants

Reaction Steps

68E (194 mg, 0.69 mmol) was suspended in 1.5 mL of toluene with 11 μL of dry DMF. Oxalyl chloride (72 μL, 0.82 mmol) was then added dropwise at 0° C. leading to a gas evolution. After the addition, the reaction was stirred at room temperature for 2 hours. After that time, the reaction mixture was concentrated. The residue was dissolved in THF. At 0° C., triethylamine (95 μL, 0.69 mmol) was added followed by trimethylsilyldiazomethane (582 μL of a 2 M solution in Et2O). The reaction was then stirred at room temperature for 16 hours. The reaction mixture was then concentrated and the residue was purified using SiO2 with CH2Cl2/AcOEt 98:2 to 85:15. An orange oil was obtained (100 mg, 48%). NMR 1H (ppm, CDCl3): 8.14 (t., J4=1.68 Hz, 1H), 8.06 (t., J4=1.60 Hz, 1H), 8.03 (t., J4=1.68 Hz, 1H), 7.59-7.55 (m, 2H), 7.46-7.34 (m, 3H), 6.51 (br.s., 1H), 6.01 (s, 1H), 3.46-3.39 (m, 2H), 1.64 (sext., J3=7.24 Hz, 2H), 0.97 (t., J3=7.37 Hz, 3H).

Provenance & Evidence