Thiophene-3-boronic acid → HCID 59375391, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-6-{[(1R)-1,2-dimethylpropyl]amino}-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one (32 mg, 0.085 mmol) in dioxane (2 mL) and Na2CO3 (1 mL, 2.0 M) were added 3-thienylboronic acid (13 mg, 0.10 mmol) and palladium tetrakistriphenylphosphine (24 mg, 0.021 mmol). The solution was degassed by bubbling nitrogen gas and heated in a microwave reactor at 150° C. for 1 hr. The resulting solution was filtered and purified by reverse phase HPLC to produce 6-{[(1R)-1,2-dimethylpropyl]amino}-9-fluoro-4-(3-thienyl)benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 9.63 (dd, 1H), 8.40 (m, 1H), 7.68 (m, 1H), 7.57 (s, 1H), 7.50 (m, 1H), 7.46 (d, 1H), 7.40 (m, 1H), 4.20 (br s, 1H), 1.98 (m, 1H), 1.24 (d, 3H), 0.93 (m, 6H). LRMS (ESI) calc'd for (C21H21FN3OS) [M+H]+, 382.1; found 382.1.

Provenance & Evidence