Potassium Phosphate, Tribasic → HCID 68328034, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-iodo-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.050 g, 0.104 mmol), 2-fluorophenylboronic acid (0.020 g, 0.145 mmol, Sigma-Aldrich), bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (3.68 mg, 5.19 μmol) and K3PO4 (0.066 g, 0.312 mmol) in 70% i-PrOH in water (1.00 mL). The mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 140° C. for 30 min. The layers were separated and the reaction vessel washed with MeOH. The organic washes were combined, filtered and purified by RP-HPLC (5-100% MeCN in H2O with 0.1% TFA over 20 min). Saturated NaHCO3 (aq.) was added to the tubes that contained the desired product. The mixture was extracted with 3/1 CHCl3/i-PrOH and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 5-(3-(2-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.005 g, 0.017 mmol, 16.30%). MS (ESI, pos. ion) m/z: 296.1 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 7.02-7.10 (m, 1H), 7.11-7.19 (m, 2H), 7.77-7.86 (m, 2H), 7.99 (d, J=2.93 Hz, 1H), 8.81-8.91 (m, 1H).

Provenance & Evidence