[H-].[Na+].[F:3][C:4]([F:17])([F:16])[C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([C:14]#[N:15])=[CH:9][CH:8]=2.I[CH3:19].O>CN(C=O)C>[CH3:19][N:6]1[C:7]2[C:12](=[CH:11][C:10]([C:14]#[N:15])=[CH:9][CH:8]=2)[CH:13]=[C:5]1[C:4]([F:3])([F:16])[F:17]Sodium hydride (60% in mineral oil) (76 mg, 1.903 mmol) was added to 2-trifluoromethyl-1H-indole-5-carbonitrile (Intermediate 3, 200 mg, 0.952 mmol) stirred in DMF (5 mL) under argon at room temperature. The reaction mixture was stirred at room temperature for 30 min and iodomethane (0.119 mL, 1.903 mmol) was then added. The reaction mixture was left to stir for a further 1 h. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL). The organic extract was washed with 1:1 water: Brine (50 mL×2), dried (MgSO4), filtered and the solvent removed to give the title compound (290 mg) which was then used in the next reaction without further purification; 1H NMR (400 MHz, CDCl3): δ 8.05 (1H, d), 7.59 (1H, dd), 7.46 (1H, d), 7.03 (1H, s), 3.90 (3H, s); m/z 225 (M+H).
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