Methanol → HCID 69880792、化合物

反応式

CO[C:3]1([S:9]([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH2:4]1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=1.[BH4-].[Na+].[CH3:28][OH:29]>>[CH3:28][O:29][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([C:11]1[CH:12]=[C:13]([NH:14][CH2:24][C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10]

参加物

反応物 4

HCID 887Methanol

HCID 103713-Pyridinecarboxaldehyde

HCID 4311764Sodium borohydride

HCID 69881808HCID 69881808、化合物

生成物 1

HCID 69880792HCID 69880792、化合物収率 82%

実験手順

3-(1-Methoxyphenylsulfinyl)aniline (145 mg, 0.59 mmol) and pyridine-3-carboxaldehyde (63 mg, 0.59 mmol) were reacted in anhydrous methanol (3.0 ml), followed by treatment with sodium borohydride (44 mg, 1.17 mmol) as previously described (Intermediate 3). Silica gel chromatography (2 mm Chromatotron® plate, eluting with 20/1 ethyl acetate/hexanes) afforded N-(3-(2-methoxyphenylsulfinyl)phenyl)pyrid-3-ylmethylamine (162 mg, 82%) as an oil. 1H NMR(400 MHz): 3.77(3H,s), 4.35(2H,br s), 6.61(1H,m), 6.83(1H,d,J=8.0), 6.96(1H,br t), 7.01-7.04(1H,m), 7.11(1H,dt,J=7.8, 1.0), 7.18(1H,t,J=7.8), 7.21-7.28(1H,br s), 7.35-7.41(1H,m), 7.63(1H,br d), 7.82(2H,dd,J=7.8, 1.5), 8.40-8.80(2H,br s); MS(ESI)m/z 339.1([M+H]+,100)