Tetrafluoro-m-phenylenediamine dihydrochloride → 2,5-Bis(2-methoxy-4-(2-pyridylimino)aminophenyl)furan

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2,5-Bis[2-methoxy-4-(2-pyridylimino)aminophenyl]furan (41, DB709) was prepared according to the procedure for 4f using diamine 3c and S-(2-naphthylmethyl)-2-pyridylthioimidate hydrobromide as starting materials. Free base: Bright yellow crystalline solid, mp 196-197° C. (EtOAc/Et2O). Yield: 75%. 1H NMR (DMSO-d6): 3.92 (s, 6H), 6.64 and 6.67 (d, 2H and s, 2H, overlapping a broad NH signal), 6.89 (s, 2H), 7.55 (dd, 2H), 7.86 (d, 2H), 7.95 (m, 2H), 8.32 (d, 2H), 8.63 (d, 2H). Dihydrochloride: brick orange solid, mp >180° C. dec. 1H NMR (DMSO-d6): 4.00 (s, 6H), 7.16 (s, 2H), 7.18 (d, 2H), 7.34 (s, 2H), 7.85 (dd, 2H), 8.13 (d, 2H), 8.22 (t, 2H), 8.49 (d, 2H), 8.89 (d, 2H), 9.39 (br s, 2H), 10.15 (br s, 2H), 11.89 (br s, 2H), MS (EI): m/z 518 (M+, 100), 414 (90.0), 371 (13.3), 310 (12.7), 267 (9.7), 155 (6.02), 104 (25.9), 77 (9.6), 43 (13.6). Anal Calcd. for C30H26N6O.2.0HCl.2.0H2O (627.51): C, H, N, Cl.

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