Potassium Carbonate → HCID 86696484, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [(S)-1-(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-pyrrolidin-3-yl]-methyl-carbamic acid tert butyl ester (83 mg, 0.21 mmol), 2-methoxypyridine-3-boronic acid (43 mg, 0.28 mmol), K2CO3 (87 mg, 0.63 mmol) and dichlorobis(triphenylphosphine)palladium(II) (7.4 mg, 0.011 mmol) in MeCN/water (3.2 ml/0.8 ml) was heated in a microwave at 150° C. for 15 min. The water layer was removed and the organic layer was diluted with MeCN and filtered. The filtrate was subjected to preparative HPLC to give the titled compound (69.3 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.50 (s, 9H) 2.11-2.29 (m, 2H) 2.84 (s, 3H) 3.40 (dd, J=10.48, 6.95 Hz, 1H) 3.46-3.53 (m, 1H) 3.67-3.74 (m, 2H) 4.08 (s, 3H) 4.94 (br. s., 1H) 6.61 (d, J=9.60 Hz, 1H) 7.03 (dd, J=7.58, 4.80 Hz, 1H) 7.77 (d, J=9.85 Hz, 1H) 8.12-8.18 (m, 2H) 8.86 (dd, J=7.58, 1.77 Hz, 1H). LRMS (ESI) m/z 425.3 [(M+H)]+, calc'd for C22H28N6O3: 424.51.

Provenance & Evidence