Picolinic acid → HCID 71236644, compound

HRID 920314Notes

Reaction equation

HRID 920314 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10](I)=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].[C:20]([O:28][CH2:29][CH3:30])(=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].N1C=CC=CC=1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20]([O:28][CH2:29][CH3:30])=[O:27])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 86676374HCID 86676374, compound

Product 1

HCID 71236644HCID 71236644, compoundYield 196.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(4-chloro-3-(trifluoromethyl)phenoxy)-2-iodopyridine (6 g, 7.06 mmol), diethyl malonate (2.261 g, 14.12 mmol) and picolinic acid (0.261 g, 2.117 mmol) in 1,4-dioxane (60 mL) were added Cs2CO3 (6.90 g, 21.17 mmol) and copper(I) iodide (0.134 g, 0.706 mmol). The reaction mixture was stirred at 80° C. for 10 hr. and then concentrated under reduced pressure. The reaction mixture was then extracted with CH2Cl2. The organic layer was separated and concentrated under reduced pressure to provide the diethyl 2-(5-(4-chloro-3-(trifluoromethyl) phenoxy)pyridin-2-yl)malonate (6 g, 77%).

Workup

  1. concentrationand then concentrated under reduced pressure
  2. extractionThe reaction mixture was then extracted with CH2Cl2
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01d9ed62b8334a588e2da865e4a759f8
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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