Sodium Carbonate → HCID 59375555, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 9-bromo-4-(cyclopropylethynyl)-6-{[(1R)-1,2,2-trimethylpropyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one (104 mg, 0.237 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (92 mg, 0.474 mmol) and 1,1′-bis(dipheylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (38.7 mg, 0.047 mmol) was added DMF (2.4 mL) and the mixture was stirred under an argon atmosphere for five minutes. Sodium carbonate (2N) (0.237 mL, 0.474 mmol) was added, and the mixture was further degassed with argon. The reaction was then heated to 130° C. for 35 minutes using microwave irradiation, then quenched with the dropwise addition to a dilute aqueous NaHCO3 solution. The crude product mixture was filtered and purified via silica gel chromatography using 0.5-10% CH3OH in CH2Cl2 as eluent to afford the title compound 4-(cyclopropylethynyl)-6-{[(1R)-1,2,2-trimethylpropyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (APCI) calc'd (C23H25N3O) [M+H]+, 360.2; found 360.2. 1H NMR (500 MHz, DMSO-d6) δ 11.33 (d, 1H), 9.80 (d, 1H), 8.51 (d, 1H), 7.75 (t, 1H), 7.58 (t, 1H), 7.49 (d, 2H), 4.88 (m, 1H), 1.54 (m, 1H), 1.21 (d, 3H), 0.98 (s, 9H), 0.87 (m, 2H), 0.70 (m, 2H).

Provenance & Evidence