Propargyl alcohol → HCID 89650617, compound

Participants

Reaction Conditions

Reaction Steps

4-anilino-6-(ethylcarbamoylamino)-N-(4-iodophenyl)pyridine-3-carboxamide (i) was prepared by coupling 4-anilino-6-(ethylcarbamoylamino)pyridine-3-carboxylic acid and 4-iodoaniline Compound (i) (50 mg, 0.10 mmol) and PdCl2(PPh3)2 (2.8 mg, 4.0 μmol) were placed in a 0.5-1.5 mL microwave vial and anhydrous DMF (1 mL) added, quickly followed by triethylamine (83 wok 0.60 mmol) and propargyl alcohol (17 μmol, 0.30 mmol). The solution was bubbled with argon for ˜3 minutes then CuI (0.38 mg, 2.0 μmol) was added. The vial was capped and mixture degassed then heated in the microwave at 100° C. for 30 minutes. The mixture was filtered on celite and then the filtrate concentrated in vacuo to give a residue that was purified by flash chromatography, eluting with methanol and DCM. The resulting product mixture was further purified by chromatography (reverse phase; ACN gradient in water), to afford Compound 135. 1H NMR (400 MHz, DMSO) δ 10.40 (br s, 1H), 9.84 (br s, 1H), 9.11 (br s, 1H), 8.57 (s, 1H), 7.94 (br s, 1H), 7.73 (br d, J=8.4 Hz, 2H), 7.45-7.36 (m, 4H), 7.27 (br d, J=7.8 Hz, 3H), 7.15 (m, 1H), 5.33-5.25 (m, 1H), 4.29 (d, J=5.0 Hz, 2H), 3.24-3.04 (m, 2H), 1.06 (t, J=7.2 Hz, 3H), [M+H]+ m/z=430.12.

Provenance & Evidence