Diisopropylamine → HCID 59375617, compound

Participants

Reaction Conditions

Reaction Steps

9-bromo-4-iodo-6-(tetrahydro-2H-pyran-4-yl)benzo[c]-1,6-naphthyridin-1(2H)-one (50 mg, 0.10 mmol), di-mu-chlorobis[(eta-allyl)palladium(II)] (2.3 mg, 6.2 μmol), copper iodide (2.4 mg, 0.012 mmol) and tri(2-furyl)phosphine (2.9 mg, 0.012 mmol) were added to a vial, followed by acetonitrile (1.0 mL), diisopropylamine (44 uL, 0.71 mmol) and 2-ethynyl pyridine (32 mg, 0.31 mmol). The resulting suspension was heated to 45° C. and stirred for four hours. The reaction mixture was diluted with 4 mL DMF and 100 uL TFA, then purified directly by preparative reverse phase HPLC eluting with an acetonitrile/water gradient (with 0.05% TFA as a modifier) to afford 9-bromo-4-(pyridin-3-ylethynyl)-6-(tetrahydro-2H-pyran-4-yl)benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (500 MHz, DMSO-D6) δ 12.38 (br s, 1H), 10.28 (s, 1H), 8.75 (s, 1H), 8.56 (d, 1H), 8.54 (d, 1H), 8.09 (s, 1H), 7.93 (overlapping t, 2H), 7.49 (dd, 1H), 4.02 (overlapping m, 3H), 3.65 (t, 2H), 2.11 (m, 2H), 1.89 (d, 2H). LRMS (ESI) calc'd for (C24H18BrN3O2) [M+H]+, 460.1; found 460.0.

Provenance & Evidence