Sodium Carbonate → HCID 67284974, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-Iodo-2-(1′-(tert-butoxycarbonyl)-2-oxo-1,2-dihydrospiro[indole-3,4′-piperidine]-5-yl)-imidazo[2,1-b][1,3,4]thiadiazole (46 mg, 0.082 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (31 mg, 0.106 mmol), PdCl2(dppf) (13 mg, 0.016 mmol) and sat Na2CO3 (0.41 mL) in DME (0.82 mL) was heated under microwave irradiation at 120° C. for 30 min. The reaction mixture was diluted with DCM and washed with H2O. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (Isolute/Flash, Sill, 0% to 5% MeOH in DCM) to give the desired product (19.5 mg, 41%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.77 min, [M+H]+ m/z 586.2; 1H NMR (300 MHz, DMSO) δ 10.90 (s, 1H), 8.87 (d, J=1.8 Hz, 1H), 8.43 (d, J=2.0 Hz, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.83 (dd, J=8.1, 1.7 Hz, 1H), 7.77 (s, 1H), 7.07 (d, J=8.2 Hz, 1H), 6.72 (s, 2H), 3.71 (s, 4H), 1.77 (m, 4H), 1.46 (s, 9H).

Provenance & Evidence