HCID 71060942, compound → HCID 71060876, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(5-chloropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate from step 3A (345 mg, 0.930 mmol) in THF (2 mL) was slowly added 1.0 M DIBAL-H/THF (4.65 mL, 4.65 mmol) at −78° C. The mixture was stirred at −78° C. for 4 h and then allowed to warm to rt. Brine was added slowly to quench the reaction. The reaction mixture was then extracted with 3×100 mL of EtOAc and the organic layers were combined, dried over sodium sulfate, and concentrated. The residue was purified using silica gel column chromatography (hexanes-60% EtOAc) to give a clean (E)-5-chloro-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide (120 mg, 0.350 mmol, 37.6% yield). LCMS (M+H)+=343.2. 1H NMR (500 MHz, chloroform-d) δ 9.81 (s, 1H), 8.56 (dd, J=2.3, 0.6 Hz, 1H), 8.25 (dd, J=8.4, 0.6 Hz, 1H), 7.87 (dd, J=8.4, 2.3 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.55 (dd, J=8.1, 2.3 Hz, 1H), 7.18 (d, J=8.2 Hz, 1H), 4.39 (s, 2H), 2.54 (t, J=7.0 Hz, 2H), 2.14 (s, 3H), 2.10 (quin, J=7.1 Hz, 2H), 2.01-1.95 (m, 2H)

Provenance & Evidence