Methylamine → 2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-methylacetamide

HRID 572692Notes

Reaction equation

HRID 572692 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:13])[N:6]([CH2:8][C:9](OC)=[O:10])[CH:7]=1.[CH3:14][NH2:15]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:13])[N:6]([CH2:8][C:9]([NH:15][CH3:14])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 28834262methyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate

Product 1

HCID 328907062-(5-bromo-2-oxopyridin-1(2H)-yl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate (0.5 g, 1.92 mmol, WO 2009134400) in 2M solution of Methyl amine in THF (5 mL) was stirred at RT for 16 h. The separated solid is collected by filtration and dried under vacuum to afford 2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-methylacetamide as off-white solid, 0.35 g (74%), 1H NMR (400 MHz, DMSO): 8.09 (1H, d, J=4.4 Hz), 7.93 (1H, d, J=2.4 Hz), 7.54 (1H, dd, J=3.0, 9.8 Hz), 6.36 (1H, d, J=9.8 Hz), 4.47 (2H, s), 2.61 (3H, d, J=4.9 Hz). ES-MS: 247.1 (M+2H).

Workup

  1. filtrationThe separated solid is collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-dd1d11926b3c4470b238918959edb734
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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