Acetamide → HCID 71735419, compound

Participants

Reaction Conditions

Reaction Steps

Sprage a mixture of 1-(5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3,3-dimethylbutyl)urea (0.200 g, 0.482 mmol), XantPhos (0.028 g, 0.048 mmol), Cs2CO3 (0.314 g, 0.964 mmol) and acetamide (0.142 g, 2.410 mmol) in dioxane (5 mL) with Ar, add Pd2(dba)3 (0.022 g, 0.024 mmol), heat at 100° C. for 7 h, then cool to RT overnight. Remove the solids via filtration through diatomaceous earth, rinse well with THF, wash the filtrate with brine (2×), dry over MgSO4, concentrate to dryness and purify via silica gel chromatography (MeOH/DCM). Triturate with MTBE, collect the solid via filtration and dry to afford the title compound (105 mg, 49%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.74 (s, 1H), 9.15 (d, J=0.8 Hz, 1H), 8.49 (s, 1H), 8.41 (d, J=2.6 Hz, 1H), 8.26 (dd, J=7.9, 2.3 Hz, 1H), 8.20 (s, 1H), 7.30 (dd, J=11.4, 8.4 Hz, 1H), 7.03 (ddd, J=8.4, 4.7, 2.3 Hz, 1H), 6.57 (t, J=5.6 Hz, 1 H), 3.11-3.05 (m, 2H), 2.57 (s, 3H), 2.15 (s, 3H), 1.36-1.31 (m, 2H), 0.88 (s, 9H); MS (ESI) m/z: 438.3 (M+H+).

Provenance & Evidence