Sodium Carbonate → 2-(2-(1-methyl-1H-pyrazol-4-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

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The mixture of 2-(2-bromobenzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (58 mg, 0.11 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole [761446-44-0] (34 mg, 0.16 mmol), (Ph3P)2PdCl2 and sodium carbonate (39 mg, 0.37 mmol) in the solvent mixture DME/H2O/EtOH (2 ml, 7:3:2) was placed in a microwave tube. The tube was sealed and the suspension was heated at 120° C. over 1 h under microwave conditions. The reaction mixture was concentrated under reduced pressure. Methanol was added and the mixture filtered through PL-thiol MP SPE cartridge (previously washed with MeOH) and evaporated to give 100 mg of a yellow oil which was purified by preparative HPLC (column Waters Sunfire C18, 5 um, 4.6×50 mm, flow 5 ml/min, solvent A: Water+0.1% TFA; Solvent B: Acetonitrile+0.1% TFA/gradient 5-100% B in 2.5 min). The product containing fractions were adjusted to pH 7 with aqueous sodium bicarbonate an extracted with ethyl acetate to yield the title compound (35 mg, 66%). [1H NMR (600 MHz, DMSO-d6) ppm 8.84 (s, 1H), 7.92 (s, 1H), 7.81 (d, J=8.1 Hz, 1H), 7.54-7.64 (m, 3H), 7.32-7.42 (m, 2H), 7.22-7.31 (m, 2H), 7.02-7.11 (m, 1H), 4.59 (s, 2H), 4.22-4.34 (m, 2H), 3.44 (t, J=11.1 Hz, 2H), 3.13 (t, J=5.9 Hz, 2H), 2.02-2.13 (m, 2H), 1.86-1.95 (m, 2H), 1.75-1.85 (m, 2H), 1.61 (d, J=13.5 Hz, 2H); LCMS RtC=3.11 min, [M+H]+=467.2].

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