Picolinic acid → HCID 71236577, compound

HRID 920307Notes

Reaction equation

HRID 920307 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[O:5][C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][N:7]=1.[C:17]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+].N1C=CC=CC=1C(O)=O>O1CCOCC1.[Cu]I>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[O:5][C:6]1[N:7]=[CH:8][C:9]([CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]([O:25][CH2:26][CH3:27])=[O:24])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 71236679HCID 71236679, compound

Product 1

HCID 71236577HCID 71236577, compoundYield 166.9%

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 suspension of 2-(3,4-difluorophenoxy)-5-iodopyridine (22 g, 41.0 mmol), diethyl malonate (6.56 g, 41.0 mmol) and Cs2CO3 (13.34 g, 41.0 mmol) in 1,4-dioxane (200 mL) was added picolinic acid (5.04 g, 41.0 mmol) and copper(I) iodide (7.80 g, 41.0 mmol). The reaction mixture was stirred at 80° C. for 10 hr. and then concentrated under reduced pressure. The residue was extracted with CH2Cl2, and then the organic layer was separated and concentrated under reduced pressure to provide diethyl 2-(6-(3,4-difluorophenoxy)pyridin-3-yl)malonate (25 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-813c99f8a6a94293a0a1d948d738deef
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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