Ethanone, 1-[1-(10H-phenothiazin-10-ylcarbonyl)-1H-indol-3-yl]- synthesis

Yield:1417560-79-2 76%

Reaction Conditions:

with dmap;triethylamine in dichloromethane at 20; for 72 h;Inert atmosphere;

Steps:

General procedure for the preparation of compounds 42, 43 (Scheme 4)

The 10H-phenothiazine-10-carbonyl chloride 44 (1.05 equiv) was dissolved in CH₂Cl₂ under inert atmosphere and added to a mixture of the corresponding indole derivative 45 or 46 (1 equiv), 4-dimethylaminopyridine (DMAP) (0.1 equiv) and Et₃N (1.3 equiv) in CH₂Cl₂. The resulting mixture was stirred for 72 hours under inert atmosphere at rt, quenched with saturated aqueous NH₄Cl solution, and washed several times with water and brine. The organic phase was dried over MgSO₄, filtrated, and the solvent evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel (EtOAc/n-heptane 5/5) to provide pure compound 42 or 43. Beigesolid; mp 178-181°C; 76% yield. IR ν_max/cm^-1: 1701, 1665, 1539,1448, 1354, 1309, 1261, 1192, 1151, 998, 747. ¹HNMR (CDCl₃, 400 MHz) δ (ppm) 2.16 (s, 3H, COCH₃), 7.14-7.24 (m, 4H, ArH), 7.30-7.41 (m, 3H, ArH),7.46-7.49 (m, 2H, ArH), 7.52-7.55 (m,2H, ArH), 8.08 (d, J = 8.4 Hz, 1H, ArH), 8.28 (d, J = 7.6 Hz,1H, ArH). ¹³C NMR (CDCl₃,100 MHz) δ (ppm) 27.2 (CH₃), 113.7 (CH), 119.9 (C),122.5 (CH), 124.4 (CH), 124.9 (2CH), 125.3 (CH), 126.3 (C), 127.0 (2CH), 127.8(2CH), 127.9 (2CH), 131.7 (2C), 132.9 (CH), 136.4 (C), 138.8 (2C), 149.8 (C),193.3 (C). Anal. calcd for C₂₃H₁₆N₂O₂S 1/5 H₂O: C, 71.19; H, 4.26; N, 7.22. Found: C, 71.41; H, 3.89; N, 7.03%.

References:

Abuhaie, Cristina-Maria;B?cu, Elena;Rigo, Beno?t;Gautret, Philippe;Belei, Dalila;Farce, Amaury;Dubois, Jo?lle;Ghinet, Alina [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 1,p. 147 - 152] Location in patent:supporting information