Bromotrimethylsilane → HCID 86659560, compound

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Reaction Steps

In a manner similar to Example 1, a mixture of {4-[3-(1-methyl-1H-imidazol-2-ylsulfanyl)-5-(thiazol-2-ylcarbamoyl)-phenoxy]-phenyl}-phosphonic acid diisopropyl ester (58 mg, 0.10 mmol) and bromotrimethylsilane (0.27 mL, 2.03 mmol) in 2 mL CH2Cl2 was stirred for 16 h at rt. The solvent evaporated, the residue dissolved in CH3CN and then the solvent evaporated, and the residue sonicated in a mixture of 1 mL CH3CN and 0.1 mL water. The resulting white solid was collected by filtration and dried under high vacuum to provide 30 mg (61%) of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 3.84 (s, 3H), 7.14 (dd, 2H, J=8, 3 Hz), 7.30 (d, 1H, J=4 Hz), 7.38 (br s, 1H), 7.55 (d, 1H, J=4 Hz), 7.72 (d, 1H, J=1 Hz), 7.72 (dd, 2H, J=12, 8 Hz), 7.76 (br s, 1H), 7.80 (t, 111, J=2 Hz), 7.88 (d, 1H, 1=1 Hz); LCMS (m/z): 489.5 [C20H17N4O5PS2+H]+. Anal. calcd. for (C20H17N4O5PS2+1.5HBr+1.5H2O): C, 37.72; H, 3.40; N, 8.80. Found: C, 37.94; H, 3.44; N, 8.58.

Provenance & Evidence