Pyridine → HCID 23521679, compound

HRID 392397Notes

Reaction equation

HRID 392397 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:11]1[CH:12]=[C:13]([NH:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=[CH:15][CH:16]=1)=[O:10].N1C=CC=CC=1.[CH2:31]([S:33](Cl)(=[O:35])=[O:34])[CH3:32]>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:11]1[CH:12]=[C:13]([N:17]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[S:33]([CH2:31][CH3:32])(=[O:35])=[O:34])[CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 69880792HCID 69880792, compound

Product 1

HCID 23521679HCID 23521679, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(3-(2-Methoxyphenylsulfinyl)phenyl)pyrid-3-ylmethylamine (159 mg, 0.44 mmol) was taken up in 1,2-dichloroethane (2.0 ml) and anhydrous pyridine (1.0 ml) and cooled under nitrogen to 0° C. Ethanesulfonyl chloride (103 mg, 0.80 mmol) is added dropwise via syringe and the reaction allowed to stir at 0° C. for thirty minutes. The ice bath is removed and the mixture stirred 88 hours at room temperature, as a matter of convenience. Solid potassium carbonate was added, the reaction stirred an additional hour, and then filtered and concentrated to a dark oil. Radial silica gel chromatography (2 mm Chromatotron® plate, eluting with 20/1 methylene chloride/methanol) afforded the title compound (16 mg, 8%). 1H NMR(400 MHz): 1.39(3H,t,J=7.3), 3.04(2H,q,J=7.3), 3.78(3H,s), 4.88(2H,s), 6.86(1H,d,J=7.8), 7.11-7.21(2H,m), 7.25-7.30(1H,m), 7.35(1H,t,J=7.8), 7.42(1H,dt,J=7.3, 2.0), 7.56-7.62(2H,m), 7.68(1H,m), 7.81(1H,dd,J=7.3, 1.5), 8.31(1H,br s), 8.46(1H,br s); MS(HRMS)m/z 431.1116([M+H]+calcd for C21H23N2O4S 431.1099).

Workup

  1. customThe ice bath is removed
  2. stirringthe mixture stirred 88 hours at room temperature, as a matter of convenience
  3. additionSolid potassium carbonate was added
  4. stirringthe reaction stirred an additional hour
  5. filtrationfiltered
  6. concentrationconcentrated to a dark oil
  7. washRadial silica gel chromatography (2 mm Chromatotron® plate, eluting with 20/1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-334709d48cb24eae8229e26400e7c07e
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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