Sodium Carbonate → HCID 86636293, compound

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), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]piperazine-1-carboxylate (45 mg, 0.12 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 9 h. The reaction mixture was concentrated, stirred in TFA (1.5 mL) for 30 min, concentrated, and purified by preparative LCMS to give the desired product (11 mg, 14%) as a white solid. LCMS for C27H27ClN7O (M+H)+: m/z=500.0. 1H NMR (300 MHz, DMSO-d6): δ 9.59 (s, 1H), 9.25 (s, 1H), 8.88 (br s, 2H), 8.21-8.18 (m, 2H), 8.00 (s, 1H), 7.67 (s, 1H), 7.35-7.29 (m, 2H), 7.25-7.16 (m, 2H), 7.00-6.80 (m, 3H), 4.55 (br s, 2H), 3.80 (br s, 4H), 3.21 (br s, 4H), 2.82 (br s, 2H).

Provenance & Evidence