2-(Tributylstannyl)pyridine → N-[4-chloro-2-[2-chloro-4-(2-pyridinyl)phenoxy]phenyl]-glycine, ethyl ester

HRID 910855Notes

Reaction equation

HRID 910855 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([Cl:23])[CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Sn](CCCC)(CCCC)CCCC>O1CCOCC1.O>[Cl:13][C:11]1[CH:10]=[CH:9][C:8]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([O:6][C:5]2[CH:21]=[CH:22][C:2]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)=[CH:3][C:4]=2[Cl:23])[CH:12]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 131729190N-[2-(4-bromo-2-chlorophenoxy)-4-chlorophenyl]-glycine, ethyl ester

Product 1

HCID 131729191N-[4-chloro-2-[2-chloro-4-(2-pyridinyl)phenoxy]phenyl]-glycine, ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The subtitle compound was prepared by using the product from example 30 step ii) (0.20 g) which was dissolved in dry dioxane (10 ml). 2-pyridyl tributyl tin (0.181 g) and palladium (0) tetrakistriphenylphosphine (0.028 g) were added and the mixture was heated at 80 C for 16 hours. The mixture was diluted with water, extracted with ethyl acetate, dried and concentrated under reduced pressure to give an oil. Yield 0.20 g.

Workup

  1. temperaturethe mixture was heated at 80 C for 16 hours
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil

Sources & evidence

ORD record
ord-ccb2979fdcbf4e859a3c080c32cc56b5
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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