m-Tolyl isocyanate → HCID 11617666, compound

Participants

Reaction Steps

A solution of Example 40 (87 mg, 0.36 mml) and 1-isocyanato-3-methylbenzene (0.046 mL, 0.36 mmol) in THF (3 mL), CH2Cl2 (3 mL) was stirred at room temperature for 5 h. The resulting precipitate was filtered off and purified via HPLC on an Agilent Zorbax Stablebond C-18 (7 micron particle size) preparative column using a solvent gradient of 20% to 100% acetonitrile in 0.1% aqueous TFA at a flow rate of 15 ml/min over 50 min, to give the 62 mg of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 2.29 (s, 3H) 3.83 (s, 3H) 6.81 (d, J=7.46 Hz, 1H) 6.92 (d, J=4.75 Hz, 1H) 7.17 (t, J=7.80 Hz, 1H) 7.26 (d, J=8.48 Hz, 1H) 7.32 (s, 1H) 7.53 (d, J=8.81 Hz, 2H) 7.65 (d, J=8.82 Hz, 2H) 8.40 (d, J=4.75 Hz, 1H) 8.67 (s, 1H) 8.90 (s, 1H). MS (ESI(+)) m/e 373 (M+H)+.

Provenance & Evidence