2-Mercaptobenzoic Acid → HCID 122436166, compound

Participants

Reaction Steps

A mixture of Pd(dba)2 (5.2 mg; 0.01 mmol; 0.05 eq.) and 1,4-bis(diphenylphosphino)butane (3.8 mg; 0.01 mmol; 0.05 eq.) in THF (1 mL) was stirred for 10 minutes then added to a solution of {2-[2-(allyl-methyl-amino)-propoxy]-4-fluoro-phenyl}-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-methanone (85 mg; 0.18 mmol; 1 eq.) in THF (3 mL) followed by 2-mercapto-benzoic acid (31 mg; 0.20 mmol; 1.1 eq.) and the reaction mixture was stirred at 60° C. for 2 hours. The solution was diluted with EA, washed with 0.1M NaOH, dried over sodium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (10 mg, 13%) as a yellow solid. 1H NMR (DMSO-d6) δ 8.25 (s, 1H), 7.39 (ddd, J=8.4, 6.8, 3.2 Hz, 1H), 7.11 (dd, J=11.4, 2.3 Hz, 1H), 6.99-6.80 (m, 1H), 4.84 (d, J=8.8 Hz, 2H), 4.55 (d, J=15.8 Hz, 2H), 4.02 (d, J=5.5 Hz, 2H), 2.97-2.86 (m, 1H), 2.84 (s, 1.5H), 2.81 (s, 1.5H), 2.62 (s, 1.5H), 2.56 (s, 1.5H), 2.25 (d, J=1.7 Hz, 3H), 0.96 (dd, J=6.5, 2.4 Hz, 3H). HPLC (max plot) 99.7%, Rt 2.82 min. UPLC/MS: (MS+) 432.3 ([M+H]+).

Provenance & Evidence