1,2-Dimethoxyethane → (S)-isopropyl (1-(3-(2-methoxy-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate

Participants

Reaction Steps

To 80 mg (0.217 mmol) of (S)-isopropyl(1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate in a microwave vial was added, 54 mg (0.326 mmol) of (2-methoxy-6-methylpyridin-3-yl)boronic acid, 92 mg (0.435 mmol) of K3PO4, 18 mg (0.022 mmol) PdCl2(dppf)2, 3 mL of DME and then 1 mL water. The resulting mixture was microwaved at 140° C. for 0.5 hr. It was diluted with EtOAc, washed with brine, and the organic layer was dried over MgSO4. It was concentrated and purified on the neutral PREP HPLC to obtain 50.6 mg of the desired product. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (d, J=6.32 Hz, 6H) 2.13-2.31 (m, 2H) 2.53 (s, 3H) 2.89 (s, 3H) 3.43 (dd, J=10.61, 7.07 Hz, 1H) 3.49-3.56 (m, 1H) 3.70-3.76 (m, 2H) 4.06 (s, 3H) 4.99 (m, 2H) 6.61 (d, J=9.85 Hz, 1H) 6.89 (d, J=7.83 Hz, 1H) 7.79 (d, J=9.85 Hz, 1H) 8.12 (s, 1H) 8.69 (d, J=7.83 Hz, 1H). LRMS (ESI) m/e 425 [(M+H)+, calcd for C22H28N6O3 424].

Provenance & Evidence