Diisopropylethylamine → HCID 71060942, compound

Participants

Reaction Steps

To a solution of 5-chloropicolinic acid (354 mg, 2.248 mmol) in dichloromethane (5 mL) was added HATU (940 mg, 2.473 mmol) and DIPEA (0.589 mL, 3.37 mmol). After stirring for 10 min, methyl 2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate from preparation J, step J1 (260 mg, 1.124 mmol) was added. The mixture was stirred at rt for 4 h. Ethyl acetate (100 mL) was added and the organic layer was washed with water. After concentration of the organic layer, the residue was purified using silica gel column chromatography (hexanes-100% EtOAc) to give methyl 2-(5-chloropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate (345 mg, 0.930 mmol, 83% yield). LCMS (M+H)+=371.3. 1H NMR (400 MHz, chloroform-d) δ 9.84 (s, 1H), 8.56 (dd, J=2.4, 0.6 Hz, 1H), 8.25 (dd, J=8.4, 0.6 Hz, 1H), 7.88 (dd, J=8.4, 2.4 Hz, 1H), 7.73 (d, J=2.3 Hz, 1H), 7.63 (dd, J=8.0, 2.3 Hz, 1H), 7.20 (d, J=8.3 Hz, 1H), 3.82 (s, 3H), 2.55 (t, J=6.5 Hz, 2H), 2.44 (s, 3H), 2.18-2.08 (m, 4H).

Provenance & Evidence