Potassium Carbonate → (1S)-1-(6-phenyl[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

A suspension of (1S)-1-(6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanol (0.289 mmol, 1 eq), phenylboronic acid (0.650 mmol, 2.3 eq), Pd(PPh3)4 (45.9 mg, 0.0397 mmol, 14 mol %), and K2CO3 (132.0 mg, 0.9551 mmol, 3.3 eq) in a 4:1 ratio of dioxane (4 mL) to H2O (1 mL) was evacuated and charged with nitrogen several times. The reaction sample was then heated conventionally at 85° C. for 1 h. CH2Cl2 and H2O were added and a standard aqueous workup was performed. The crude material was purified by pTLC [Silicycle, 1000 μM, 20×20 plate], which required two developments in a 3% MeOH in EtOAc solvent system. 1H NMR (400 MHz, CDCl3): δ=1.93 (d, J=6.6 Hz, 3H), 3.00 (br s, 1H), 5.64 (q, J=6.6 Hz, 1H), 7.53-7.61 (m, 3H), 7.66 (d, J=9.9 Hz, 1H), 7.95-8.01 (m, 2H), 8.25 (d, J=9.9 Hz, 1H). MS (ES+): m/z 241.08 (100) [MH+]. HPLC: tR=2.51 min (ZQ3, polar—5 min).

Provenance & Evidence