Water → HCID 118274327, compound

Participants

Reaction Steps

To a solution of Example 41B (18.49 g, 73.0 mmol) in N,N-dimethylformamide (146 mL) at room temperature under nitrogen was added sodium hydride (4.38 g, 110 mmol) in portions. The mixture was stirred for 30 minutes and p-toluenesulfonyl chloride (15.31 g, 80 mmol) was added in portions over 10 minutes. The mixture was stirred overnight at room temperature, poured into water and filtered. The solid was washed with heptanes and placed in a vacuum oven overnight at 50° C. The residue was taken up in dichloromethane/methanol and concentrated to give a solid containing ˜10% unreacted starting material. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (d, J=5.3 Hz, 1H), 8.01 (d, J=8.4 Hz, 2H), 7.76 (d, J=10.4 Hz, 1H), 7.71 (s, 1H), 7.61 (d, J=5.5 Hz, 1H), 7.41 (d, J=8.1 Hz, 2H), 7.31-7.25 (m, 2H), 4.10 (s, 2H), 2.89 (s, 3H), 2.33 (s, 3H). MS (ESI+) m/z 408.5 (M+H)+.

Provenance & Evidence