Picolinic acid → 6-(2-Chloro-phenoxy)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

HRID 1475403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475403
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14](Br)[N:13]=[CH:12][C:11]=2[C:10]([CH3:19])([CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27].N1C=CC=CC=1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([O:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[Cl:20])[N:13]=[CH:12][C:11]=2[C:10]([CH3:19])([CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 1018Picolinic acidHCID 72452-ChlorophenolHCID 62657Potassium Phosphate, TribasicHCID 86724003Tert-butyl 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-C]pyridine-1-carboxylate

Produkt 1

HCID 709805436-(2-Chloro-phenoxy)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl esterAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (150 mg, 0.46 mmol), 2-chlorophenol (0.071 mL, 0.69 mmol), CuI (17 mg, 0.046 mmol), picolinic acid (23 mg, 0.092 mmol) and potassium phosphate (195 mg, 0.92 mmol) in DMSO (1 mL) was stirred at 85° C. overnight. The mixture was allowed to cool and then partitioned between EtOAc and water. The organic extract was washed with brine, dried (MgSO4) and evaporated in vacuo. Chromatography (SiO2; gradient elution with 2-10% ethyl acetate in petrol) gave the title compound (143 mg). MS: [M+H]+=375.

Aufarbeitung

  1. temperatureto cool
  2. custompartitioned between EtOAc and water
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. washChromatography (SiO2; gradient elution with 2-10% ethyl acetate in petrol)

Quellen und Nachweise

ORD-Eintrag
ord-388cf3889889497b9429517ff1bb5d84
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018214B2

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