HCID 90403622, compound → HCID 86268465, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Example C1 (0.20 g, 0.551 mmol), Example C2 (0.254 g, 1.158 mmol) and satd. NaHCO3 (1.1 mL) in dioxane (4.4 mL) was sparged with Ar under sonication, treated with Pd(PPh3)4 (0.064 g, 0.055 mmol), sparged again with Ar, heated at 80° C. for 3 h, then 90° C. for 1.5 h. The mixture was cooled to RT, diluted with EtOAc and filtered through diatomaceous earth. The filtrate was concentrated to dryness and purified via silica gel chromatography (MeOH/DCM). The material was further purified via reverse-phase silica gel chromatography (MeCN/H2O with 0.1% TFA). Pure fractions were combined and concentrated under reduced pressure. The aqueous residue was neutralized with satd. Na2CO3 and the solid collected via filtration, dissolved in MeCN/H2O, frozen and lyophilized to afford N-((6-methyl-5-((6′-methyl-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (150 mg, 65%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.15 (s, 1H), 10.39 (s, 1H), 9.08 (d, J=2.4 Hz, 1H), 8.52 (d, J=5.7 Hz, 1H), 8.26 (dd, J=8.1, 2.4 Hz, 1H), 7.91 (m, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.57 (d, J=2.4 Hz, 1H), 7.32 (d, J=8.2 Hz, 1H), 6.78 (dd, J=5.7, 2.4 Hz, 1H), 2.49 (s, 3H), 2.26 (s, 3H), 1.20 (s, 9H); MS (ESI) m/z: 420.2 (M+H+).

Provenance & Evidence