Picolinic acid → HCID 66653896, compound

HRID 588254Notes

Reaction equation

HRID 588254 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)([CH3:15])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].I[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=1[CH3:32].N1C=CC=CC=1C(O)=O>CS(C)=O.[Cl-].[Na+].O.[Cu]I>[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][C:11]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=3[CH3:32])=[CH:20][CH:21]=2)([CH3:15])[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 1018Picolinic acidHCID 1416452,3-DimethyliodobenzeneHCID 67032456HCID 67032456, compound

Product 1

HCID 66653896HCID 66653896, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed solution of 3-[2-(4-hydroxy-phenyl)-2-methyl-morpholin-4-yl]-propionic acid tert-butyl ester (1.07 g; 3.33 mmol), and 3-iodo-o-xylene (0.97 g; 4.16 mmol) in DMSO (20 mL) was added picolinic acid (82 mg; 0.67 mmol), CuI (63.4 mg; 0.33 mmol) and powdered (1.41 g; 6.66 mmol). The resulting mixture was heated for 24 h, at 90° C. After cooling to room temperature, brine was added and the mixture extracted with CH2Cl2. The combined layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1) to afford 3-{2-[4-(2,3-dimethyl-phenoxy)-phenyl]-2-methyl-morpholin-4-yl}-propionic acid tert-butyl ester (1.32 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture extracted with CH2Cl2
  3. dry with materialThe combined layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1)

Sources & evidence

ORD record
ord-eaa9635784b841049bbe869c80e807ca
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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