ClC1C(C[F:9])=CC=CN=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.CC[N:22]([CH:26](C)C)C(C)C.[CH2:29](O)[CH2:30][CH2:31][CH3:32]>CN(C1C=CN=CC=1)C>[F:9][C:32]1[C:26]([NH:17][CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[N:22][CH:29]=[CH:30][CH:31]=1A mixture of commercially available 2-chloro-3-fluoromethylpyridine (10.53 g, 80 mmol), 4-methoxybenzylamine (12.5 mL, 96 mmol), DIPEA (16.5 mL, 96 mmol) and DMAP (150 mg) in n-butanol (20 mL) was refluxed (oil bath temp. 140° C.) for 12 days. Concentrated in vacuum and directly subjected to chromatography. Silica gel column chromatography gave the title compound as a yellow liquid (6.3 g, 34%). MS (ISP) 233.1 [(M+H)+].
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