Reaction Steps
A mixture of 5-(2-chloro-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (Example 1, Step A, 0.300 g, 0.873 mmol), 3,3,4,4-tetramethyl-pyrrolidine; hydrochloride (0.571 g, 3.49 mmol), K2CO2 (0.724 g, 5.234 mmol), and KI (0.014 g, 0.087 mmol) in 17.5 mL of acetonitrile was heated at reflux for 24 hours. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 (50 mL) and washed with water (2×20 mL). The organic layer was dried over MgSO4 and concentrated to give 0.379 g (42.0%) of a white solid: mp 181-182° C.;IR(KBr)3283, 2961, 1671, 1652, 1457, 1171, 1074 cm−1; 1HNMR (400 MHz, DMSO-d6) δ 0.85 (s, 12H, NCH2C(CH3)2), 2.46 (s, 3H, CCH3), 2.60 (s, 4H, NCH2C(CH3)2), 2.81-2.84 (m, 2H, OCH2CH2),3.83 (t, J=6.12 Hz, 2H, OCH2CH2), 5.27 (s, 2H, OCH2Ar), 6.67 (dd, J=8.31, 3.20 Hz, 1H, ArH), 7.20 (d, J=8.40 Hz, 1H, ArH), 7.23-7.40 (m, 4H, ArH), 7.46 (d, J=7.89 Hz, 2H, ArH), 11.70 (s, 1H, NH); MS(APCI+): m/z 435.3 (MH+). Anal. Calcd for C27H34N2O3: C, 74.62; H, 7.89; N, 6.45. Found: C, 74.31; H, 7.98; N, 6.19.
