[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH:5]=O.Cl.[NH2:21][OH:22].C([BH3-])#N.[Na+].[C:27]([OH:30])(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][N:21]([OH:22])[CH:27]=[O:30]A solution of 3,5-dichloro-4-(4-methoxyphenoxy)benzaldehyde (170 mg, 0.572 mmol) and hydroxylamine hydrochloride (48 mg, 0.687 mmol) in 1 ml of pyridine was stirred for 1 h then all volatiles were removed in vacuo. The resulting imine intermediate was treated with sodium cyanoborohydride (122 mg, 1.944 mmol) in 2 ml of glacial acetic acid for 5 h. The reaction mixture was then quenched with water and neutralized with sodium bicarbonate powder, extracted with ethyl acetate and dried (sodium sulfate). The resulting 3,5-dichloro-N-hydroxy-4-(4-methoxyphenoxy)benzyl amine was converted to the title compound using the method described in example 1c (50 mg, 26%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.34 (s, 2H), 6.82 (d, j=8.8 Hz, 2H), 6.76 (d, j=8.8 Hz, 2H), 4.64 (s, 2H), 3.76 (s, 3H). M+1=342.
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