Bromotrimethylsilane → HCID 67994725, compound

Participants

Reaction Steps

In a similar manner to Example 1, a mixture of diethyl {2-[3-isopropoxy-5-(4-methanesulfonyl-phenoxy)-benzoylamino]-pyrazin-5-ylmethyl}phosphonate (29 mg, 0.05 mmol) and bromotrimethylsilane (0.13 mL, 1.0 mmol) in 1 mL of CH2Cl2 was stirred for 16 h at rt and the solvents evaporated. The residue was sonicated in 1 mL of CH3CN, the solvent evaporated, the residue sonicated in 1 mL CH3CN and 2 mL water, the solution concentrated by evaporation followed by lyophilization to provide 28 mg (76%) of the title compound as an amorphous solid. 1H NMR (500 MHz, DMSO-d6): δ 1.31 (d, 6H, J=6 Hz), 3.21 (s, 3H), 3.23 (d, 2H, J=22 Hz), 4.78 (septet, 1H, J=6 Hz), 6.97 (t, 1H, J=2 Hz), 7.25 (d, 2H, J=8 Hz), 7.36 (t, 1H, J=2 Hz), 7.52 (t, 1H, J=2 Hz), 7.95 (d, 2H, J=8 Hz), 8.39 (t, 1H, J=2 Hz), 9.25 (d, 1H, J=1 Hz), 11.13 (s, 1H); LCMS (m/z): 522.4 [C22H24N3O8PS+H]+. Anal. calcd. for (C22H24N3O8PS+2HBr+3H2O): C, 35.84; H, 4.37; N, 5.70. Found: C, 35.59; H, 4.19; N, 5.41.

Provenance & Evidence