Sodium bis(trimethylsilyl)amide → 2-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-thiophen-2-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

Participants

Reaction Steps

To a stirring solution of 200 mg (0.43 mmol) of 2-(2,4-dioxo-5-thiophen-2-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Part A, in 5 mL DMF at 0° C. is added 1.04 mL (0.52 mmol, 1.2 equiv) of NaN(TMS)2 in toluene. The resulting solution is stirred 5 min and 162 mg (0.52 mmol, 1.2 equiv) of 3-bromomethyl-1-tert-butoxycarbonyl-1H-indazole is added. The resulting solution is stirred 16 h at RT, poured into 100 mL Et2O/EtOAc (1:1), washed with H2O (3×50 mL). The organic layer is separated, dried (MgSO4), and the solvents removed in vacuo to afford 280 mg of the crude title compound: low resolution MS (FAB) m/e 694 (MH+).

Provenance & Evidence