Cesium carbonate → 1-((1H-indol-4-yl)methyl)-9-(benzo[d]oxazol-2-yl)-1,9-diazaspiro[5.5]undecan-2-one

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Reaction Steps

Cs2CO3 (430 mg, 1.32 mmol) was added to a stirred solution of 9-(benzo[d]oxazol-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one (250 mg, 0.44 mmol) in methanol (10 mL) and stirring was continued for 18 h at 78° C. The reaction mixture was concentrated, water was added to the residue and extracted with ethyl acetate (2×50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by reversed phase HPLC (column Zorbax eclipseXDB C18 21.2×150 mm 5 ♀m, flow 20 mL/min, eluent: gradient water/acetonitrile) to yield the title compound (126 mg, 69%). [1H NMR (400 MHz, CDCl3) ♀ ppm 8.30 (br s, 1H), 7.36-6.96 (m, 7H), 6.78 (d, 1H), 6.46 (m, 1H), 4.95 (s, 2H), 4.16 (dd, 2H), 3.18 (t, 2H), 2.65 (t, 2H), 2.20-2.05 (m, 4H), 1.95-1.88 (m, 2H), 1.75-1.61 (m, 2H); LCMS RtE=1.32 min, [M+H]+=415.1].

Provenance & Evidence