C([Li])(C)(C)C.CC[O:8][CH2:9][CH3:10].Br[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1C)[NH:17][CH:16]=[C:15]2[CH3:22]>CN(C=O)C>[CH3:22][C:15]1[C:14]2[C:18](=[CH:19][C:20]([CH3:12])=[C:10]([CH:9]=[O:8])[CH:13]=2)[NH:17][CH:16]=1tert-Butyl lithium (16.7 mL, 28.3 mmol, 1.7 M in pentanes) was added to a dry ether (20 mL) solution of 5-bromo-3,6-dimethyl-1H-indole (1.27 g, 5.67 mmol) at −78° C. under Argon. The mixture was stirred at 0° C. for 30 min then cooled to −78° C. DMF (18 mL) was added and the mixture was stirred at 0° C. for 1 h. The reaction was quenched with cold, saturated NH4Cl solution at −78° C. The mixture was diluted with ether and hexane, washed with brine, dried and evaporated. Crystallization from a CH2Cl2/hexane mixture afforded the title compound (810 mg 82%). 1H NMR (300 MHz, CDCl3) 10.29 (s, 1H), 8.06 (s, 1H), 8.00 (s, br, 1H), 7.15 (1s, 1H), 6.97 (s, 1H), 2.76 (s, 3H), 2.36 (s, 3H).
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