Ethyl 3-amino-6-bromopicolinate → Ethyl 3-amino-6-cyanopyridine-2-carboxylate

HRID 1260308Notes

Reaction equation

HRID 1260308 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8](Br)[N:7]=1)=[O:5])[CH3:2].[Cu][C:15]#[N:16]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([C:15]#[N:16])[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25137688Ethyl 3-amino-6-bromopicolinateHCID 178418546HCID 178418546, compound

Product 1

HCID 58368044Ethyl 3-amino-6-cyanopyridine-2-carboxylateYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-6-bromo-pyridine-2-carboxylic acid ethyl ester (40 mg, 163 μmol) and copper(I) cyanide (29.2 mg, 326 μmol) in DMF (800 μL) was heated in the microwave at 220° C. for 8 min. The reaction mixture was filtered through diatomaceous filter-aid and the crude product was purified by preparative HPLC to afford the title compound as off-white solid (8.3 mg, 26.6%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. filtrationthrough diatomaceous filter-aid
  3. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e28363ed474a465989559d9c52a07b63
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

Loading…