Methyl iodide → 3-bromo-1-methyl-5-(morpholine-4-carbonyl)pyridin-2(1H)-one

HRID 58044Notes

Reaction equation

HRID 58044 reaction equation
[Br:1][C:2]1[C:3](=[O:16])[NH:4][CH:5]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])[CH:7]=1.IC.[C:19](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[C:3](=[O:16])[N:4]([CH3:19])[CH:5]=[C:6]([C:8]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89783090HCID 89783090, compound

Product 1

HCID 897830313-bromo-1-methyl-5-(morpholine-4-carbonyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-bromo-5-(morpholine-4-carbonyl)pyridin-2(1H)-one (430 mg, 1.498 mmol), iodomethane (0.112 mL, 1.797 mmol), and potassium carbonate (207 mg, 1.498 mmol) in DMSO (5 mL) was stirred at room temperature overnight. The reaction mixture was subsequently filtered and purified via preparative HPLC, eluting with a gradient of 30-70% ACN in H2O (containing 10 mM NH4HCO3) to give the title compound.

Workup

  1. filtrationThe reaction mixture was subsequently filtered
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 30-70% ACN in H2O (containing 10 mM NH4HCO3)

Sources & evidence

ORD record
ord-79b538c47137425f8ba43adc92985a07
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

Loading…