Sodium Carbonate → 6-Chloro-19-pyridin-4-yl-14-oxa-2,4,8,23-tetraazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene bis(trifluoroacetate)

Participants

Reaction Conditions

Reaction Steps

A solution of 19-bromo-6-chloro-14-oxa-2,4,8,23-tetraazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaene trifluoroacetate (40 mg, 96 μmol), 4-pyridinylboronic acid (13 mg, 0.11 mmol), and 2 M sodium carbonate (0.14 mL, 0.29 mmol) in toluene (0.36 mL) and ethanol (0.36 mL) was degassed with nitrogen, treated with tetrakis(triphenylphosphine)palladium(O) (8 mg, 6.7 μmol), and heated at 85° C. for 12 h. The reaction mixture was concentrated and purified by preparative LCMS to give the desired product (4 mg, 7%) as a white solid. LCMS for C23H19ClN5O (M+H)+: m/z=416.0. 1H NMR (400 MHz, DMSO-d6): δ 9.62 (s, 1H), 9.20 (s, 1H), 8.90 (br s, 2H), 8.19 (s, 1H), 8.13-8.05 (m, 3H), 7.65 (s, 1H), 7.52 (s, 1H), 7.45 (s, 1H), 7.24 (dd, J=8.2, 8.0 Hz, 1H), 6.94-6.86 (m, 2H), 4.57-4.54 (m, 2H), 2.85-2.78 (m, 2H).

Provenance & Evidence