Sodium Thiosulfate → 5-iodo-1-(4-methoxybenzyl)-3,4-dihydropyridin-2(1H)-one

Temperature

-78 °C

1-(4-methoxybenzyl)-3,4-dihydropyridin-2(1H)-one (2 g, 9.21 mmol) was dissolved in MeOH (90 mL) and cooled to −78° C. ICl (13.81 ml, 13.81 mmol) was added slowly and the mixture agitated for 1 h and then Sat′d Na2S2O3 was added and the mixture was agitated until room temperature was observed. The solvent was evaporated in vacuo. The residue was dissolved in DCM and washed with Sat′d Na2S2O3 and then with water and dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in toluene (40 mL) and treated with Trifluoroacetic acid (100 uL) and heated immediately to 145° C. for 15 min and then cooled to 0° C. and ET3N (5 mL) was added. The mixture was agitated for 1 h and concentrated in vacuo and then the residue purified by flash chromatography (0-20% EtOAc/heptane) to afford the desired product as a gummy syrup. LCMS (m/z): (MH+), 344.1, 0.88 min.

1. stirringthe mixture was agitated until room temperature
2. customThe solvent was evaporated in vacuo
3. dissolutionThe residue was dissolved in DCM
4. washwashed with Sat′d Na2S2O3
5. dry with materialwith water and dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in toluene (40 mL)
9. additiontreated with Trifluoroacetic acid (100 uL)
10. temperatureheated immediately to 145° C. for 15 min
11. temperaturecooled to 0° C.
12. additionET3N (5 mL) was added
13. stirringThe mixture was agitated for 1 h
14. concentrationconcentrated in vacuo
15. customthe residue purified by flash chromatography (0-20% EtOAc/heptane)

ORD record

ord-d196c10a66fa438eaab1fbd32ffa21a1

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2