Cesium carbonate → 5-bromo-1-(2-(methylsulfonyl)ethyl)-3-morpholinopyridin-2(1H)-one

HRID 594053Notes

Reaction equation

HRID 594053 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5](=[O:8])[NH:6][CH:7]=1.[CH3:15][S:16]([CH:19]=[CH2:20])(=[O:18])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>>[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5](=[O:8])[N:6]([CH2:20][CH2:19][S:16]([CH3:15])(=[O:18])=[O:17])[CH:7]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 19354Methyl vinyl sulfoneHCID 904098535-Bromo-3-morpholinopyridin-2-ol

Product 1

HCID 904082125-bromo-1-(2-(methylsulfonyl)ethyl)-3-morpholinopyridin-2(1H)-oneYield 98%

Procedure

Method 1 was followed using 5-bromo-3-morpholinopyridin-2(1H)-one (1.0 equiv.), (methylsulfonyl)ethene (1.2 equiv.) and cesium carbonate (1.2 equiv.) at room temperature to give 5-bromo-1-(2-(methylsulfonyl)ethyl)-3-morpholinopyridin-2(1H)-one in 98% yield. 1H NMR (400 MHz, <cdcl3>) δ ppm 2.92 (s, 3H) 3.09-3.23 (m, 4H) 3.53 (t, J=6.65 Hz, 2H) 3.78-3.96 (m, 4H) 4.32 (t, J=6.65 Hz, 2H) 6.69 (s, 1H) 7.23 (d, J=2.35 Hz, 1H). LCMS (m/z) (M+H)=365.1/366.9, Rt=0.57 min.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-1d51f54bb85749f9a496fe44b5695ce7
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

Loading…