Methanol → HCID 69880792, compound

HRID 392396Notes

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)

Workup

washSilica gel chromatography (2 mm Chromatotron® plate, eluting with 20/1 ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-f0974ac905304e0284b6cff8399a43ab
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800651B2

Reaction notes

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