Ammonia → 5-(2-Methoxy-ethoxy)-3-methyl-pyridine-2-carboxylic acid amide

HRID 925469Notes

Reaction equation

HRID 925469 reaction equation
C(O[C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9](Br)=[CH:8][N:7]=1)=[O:5])C.[CH3:14][O:15][CH2:16][CH2:17][OH:18].[H-].[Na+].[NH3:21]>CN(C=O)C.CCO.[Cu]I>[CH3:14][O:15][CH2:16][CH2:17][O:18][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([C:4]([NH2:21])=[O:5])=[N:7][CH:8]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 53418426Ethyl 5-bromo-3-methylpicolinate

Product 1

HCID 895003265-(2-Methoxy-ethoxy)-3-methyl-pyridine-2-carboxylic acid amide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-Bromo-3-methyl-pyridine-2-carboxylic acid ethyl ester (3.3 g, 13.52 mmol) and CuI (0.515 g, 2.70 mmol) were dissolved in 2-methoxy-ethanol (10.29 g, 135 mmol) and DMF (2.5 ml). NaH (60%, 0.541 g, 13.52 mmol) was carefully added and the reaction mixture was warmed to 110° C. for 8 h. The reaction mixture was allowed to cool to rt and NH3 in EtOH (10%, 30 ml) was added. The reaction mixture was placed in an autoclave and heated to 100° C. for 20 h. The reaction mixture was cooled to rt, concentrated and purified by column chromatography (silica gel; DCM/0-4% i-Propanol) to give the desired product (1 g, 4.52 mmol).

Workup

  1. temperatureto cool to rt
  2. temperatureheated to 100° C. for 20 h
  3. temperatureThe reaction mixture was cooled to rt
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica gel; DCM/0-4% i-Propanol)

Sources & evidence

ORD record
ord-aca971e5760343c79024fcf1194cee85
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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