Cesium carbonate → HCID 118271680, compound

Participants

Reaction Conditions

Reaction Steps

6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (500 mg, 1.217 mmol), (R)-1-(1-phenylethyl)urea (400 mg, 2.434 mmol), cesium carbonate (1023 mg, 3.14 mmol) and chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-i-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (58.3 mg, 0.073 mmol) were charge in a 40 mL vial with dioxane (11 ml). System was degassed and stirred at 100° C. for 3 hours. Reaction mixture was evaporated in vacuo and purified by normal phase column chromotography eluting with hexane/EtOAc (0-50%) affording (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (333 mg, 0.618 mmol, 50.8% yield) as an off white solid. 1H NMR (500 MHz, dmso) δ 8.82 (s, 1H), 8.51 (s, 1H), 8.32 (bs, 1H), 7.38-7.13 (m, 19H), 6.49 (s, 1H), 5.88 (s, 2H), 4.85-4.75 (m, 1H), 1.35 (d, 3H). MS ESI calc'd. For C34H30N6O[M+H]+ 539. found 539.

Provenance & Evidence