m-Toluidine → HCID 11175937, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 127B (70 mg, 0.27 mmol) and triethylamine (0.046 mL, 0.32 mmol) in DMF (8 mL) was treated with diphenylphosphorylazide (0.072 mL, 0.32 mmol), heated to 80° C. for 2 hours, cooled to room temperature, and treated with 3-methylaniline (0.03 mL, 0.27 mL). The resulting mixture was heated to 80° C. for 2 hours, cooled to room temperature, diluted with water, and extracted with dichloromethane and ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by silica gel chromatography, with 3% methanol/dichloromethane to give the desired product (13% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.29 (s, 3H), 4.58 (s, 2H), 6.63 (d, 1H, J =4.2 Hz), 6.82 (d, 1H, J=6.9 Hz), 7.14–7.27 (m, 3H), 7.34 (s, 1H), 7.48–7.58 (m, 2H), 7.75–7.79 (m, 1H), 8.73 (s, 1H), 8.77 (s, 1H), 9.86 (s, 1H); MS (ESI(+)) m/e 364.0 (M+H)+.

Provenance & Evidence