Water → HCID 66815272, compound

HRID 630239Notes

Reaction equation

HRID 630239 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:14][Zn]C.O>O1CCOCC1>[Cl:13][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([CH3:14])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 46311456Ethyl 3-bromo-5-chloropyridine-4-carboxylateHCID 178477796HCID 178477796, compound

Product 1

HCID 66815272HCID 66815272, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of ethyl 3-bromo-5-chloropyridine-4-carboxylate (28 g, 105 mmol) in dioxane (300 mL) in a 1 L round bottom flask was added dimethylzinc (105 mL, 1.0 M in hexane) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (II) dichloromethane complex (1.3 g, 1.6 mmol). The resulting mixture was heated at 60° C. for 20 hours. After cooling, the reaction mixture was poured into cold water (500 mL) and extracted with dichloromethane (3×200 mL). After evaporation of the solvent, the crude product was filtered through a silica pad (10 cm) with 20% ethyl acetate in hexane (400 mL), and the solvent was evaporated. The oily ethyl 3-chloro-5-methylpyridine-4-carboxylate (20 g, 90% yield) was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane (3×200 mL)
  3. customAfter evaporation of the solvent
  4. filtrationthe crude product was filtered through a silica pad (10 cm) with 20% ethyl acetate in hexane (400 mL)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-83d31a9fc7d648c68405ff10999a6061
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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