2-Amino-5-chloropyridine → methyl 3-(5-chloro-2-iminopyridin-1(2H)-yl)-2-oxobutanoate hydrobromide

HRID 627697Notes

Reaction equation

HRID 627697 reaction equation
[Br:1][CH:2]([CH3:9])[C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=1>COCCOC>[BrH:1].[Cl:17][C:14]1[CH:15]=[CH:16][C:11](=[NH:10])[N:12]([CH:2]([CH3:9])[C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5])[CH:13]=1

Participants

4

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 11183175Methyl 3-bromo-2-oxobutanoate

Product 1

HCID 86728148methyl 3-(5-chloro-2-iminopyridin-1(2H)-yl)-2-oxobutanoate hydrobromideYield 62%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of methyl 3-bromo-2-oxobutanoate (8.26 g, 42.4 mmol) in DME (33 mL) at room temperature was added 2-amino-5-chloropyridine (5.45 g, 42.4 mmol). The reaction mixture was stirred at room temperature for 20 h. The solid was collected by filtration, washed with EtOAc (2×), and dried under high vacuum to give methyl 3-(5-chloro-2-iminopyridin-1(2H)-yl)-2-oxobutanoate hydrobromide (8.51 g, 26.3 mmol, 62% yield) as a white solid.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with EtOAc (2×)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-c20f4f2d535545609f935574bdec11e5
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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