[H-].[Na+].[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[CH2:16]([N:8]([CH2:6][CH2:5][CH2:4][CH2:10][CH3:9])[C:7]1[CH:9]=[CH:10][C:4]([Br:3])=[C:5]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)[CH2:17][CH2:18][CH2:19][CH3:20]Sodium hydride (480 mg, 1.5 eq.) was added to a solution of 4-bromo-3-trifluoromethylaniline (1.92 g, 5 mmol) and 1-bromopentane (3 mL, 3 eq.) in dimethylformamide (10 mL) at 0° C. After 1 hour a further (320 mg, 1 eq.) of sodium hydride was added and the reaction was left overnight. The reaction was heated to 50° C. and left overnight. The reaction was quenched with methanol and partitioned between water and petroleum ether. The organic extract was concentrated under reduced pressure and the residue was purified via flash column chromatography using petroleum ether as eluent to give N,N-Dipentyl-4-bromo-3-trifluoromethylaniline (3) (2.84 g. 93%). 1H NMIR (CDCl3) 6 7.34 (d, IH, ArH); 6.80 (d, 1H, ArH); 6.52 (dd, 1H, ArH); 3.18 (t, 4H, 2×NCH2); 0.86 (t, 6H, CH˜1b). TLC (silica gel): RI˜0.55 (petroleum ether).
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