Water → HCID 87126801, compound

HRID 1677719Notes

Reaction equation

HRID 1677719 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH3:12][C:13]([S@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14].O.S([O-])([O-])(=O)=O.[Mg+2]>ClC(Cl)C.ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[N:7]=[CH:6][C:5](/[C:8](=[N:18]/[S:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])/[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 59278472HCID 59278472, compound

Product 1

HCID 87126801HCID 87126801, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 1-(6-bromo-pyridin-3-yl)-propan-1-one (11.8 g, 55.1 mmol), (R)-(+)-2-methyl-2-propanesulfinamide (8.0 g, 66 mmol) and titanium isopropoxide (18.0 mL, 61.4 mmol) in dichloroethane (65 mL) was warmed at reflux for 2 days. The reaction was monitored by TLC (ethyl acetate-hexanes 2:8) indicating a new more polar product than starting ketone, however ketone was still evident. The mixture was diluted with first dichloromethane (600 mL) and then water (15 mL) was added. The mixture was stirred for 10 minutes and then magnesium sulfate added. The mixture was filtered through diatomaceous earth and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-40% ethyl acetate in hexanes and then a gradient of 0-40% ethyl acetate in dichloromethane to afford 2-methyl-propane-2-sulfinic acid [1-(6-bromo-pyridin-3-yl)-prop-(E)-ylidene]-amide.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 2 days
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient of 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0c21d7e445774054989bf8206f08da38
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

Loading…