Cesium fluoride → N-[4-chloro-2-[2-chloro-4-(5-pyrimidinyl)phenoxy]phenyl]-glycine, ethyl ester

HRID 910854Notes

Reaction equation

HRID 910854 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.[F-].[Cs+].[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1>O1CCOCC1.Cl.[Cl-].[Cl-].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Pd+2]>[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:30]3[CH:31]=[N:26][CH:27]=[N:28][CH:29]=3)=[CH:3][C:4]=2[Cl:23])[CH:12]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 131729190N-[2-(4-bromo-2-chlorophenoxy)-4-chlorophenyl]-glycine, ethyl ester

Product 1

HCID 131729189N-[4-chloro-2-[2-chloro-4-(5-pyrimidinyl)phenoxy]phenyl]-glycine, ethyl ester

Reagents, catalysts & solvents 3

HCID 178478644HCID 178478644, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 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). Cesium fluoride (0.15 g) followed by pyrimidine-5-boronic acid (0.058 g) and Palladium(diphenylphosphinoferrocene) dichloride (0.017 g) were added and the mixture was heated at 80 C for 10 hours. The mixture was diluted with 2M HCl, extracted with ethyl acetate, dried and concentrated under reduced pressure to give an oil. Yield 0.20 g.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated at 80 C for 10 hours
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil

Sources & evidence

ORD record
ord-07c0e2887a974e78b7f2c6f4eddd9aa9
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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