Water → 2-[3-(6-Fluoro-1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 427 mg of 2-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl) acetamide in 5 mL of dry DMF at 0° C. is added 2.2 mL of a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene. The reaction mixture is stirred for 30 min at 0° C. and a solution of 329 mg of 3-Bromomethyl-6-fluoro-1-tert-butoxycarbonyl indazole in 2 mL of dry DMF is added dropwise. The reaction mixture is stirred overnight at RT, poured into water and the product extracted with ethyl acetate (2×15 mL). The solvent is removed in vacuo and the residue is purified by silica gel flash column chromatography (MeOH 1%:CHCl3 99%) to afford 410 mg of the title compound: 1H NMR (400 MHz, CDCl3) δ7.85-6.91 (m, 17H), 5.01 (m, 1H,J=6.8), 4.22 (m, 3H), 3.81 (dd, 1H, J=16.5, 8.9), 3.51 (dd, 1H, J=16.5, 4.7), 1.68 (s, 9H), 1.07 (d, 6H, J=6.8).

Provenance & Evidence