Methanol → HCID 69880792, compound

Reaction equation

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]

Participants

Reactant 4

HCID 887Methanol

HCID 103713-Pyridinecarboxaldehyde

HCID 4311764Sodium borohydride

HCID 69881808HCID 69881808, compound

Product 1

HCID 69880792HCID 69880792, compoundYield 82%

Procedure

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)