Cesium carbonate → Methyl 1-cyclopentyl-6-oxo-5-(pyrrolidin-1-yl)-1,6-dihydropyridine-3-carboxylate

HRID 1696277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696277
Br[C:2]1[C:7](=[O:8])[N:6]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:9]1([N:6]2[C:7](=[O:8])[C:2]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:3][C:4]([C:14]([O:16][CH3:17])=[O:15])=[CH:5]2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 15946267Methyl 5-bromo-1-cyclopentyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Produkt 1

HCID 66845136Methyl 1-cyclopentyl-6-oxo-5-(pyrrolidin-1-yl)-1,6-dihydropyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of methyl 5-bromo-1-cyclopentyl-6-oxo-1,6-dihydropyridine-3-carboxylate (100 mg, 0.33 mmol), pyrrolidine (33 uL, 0.40 mmol), cesium carbonate (150 mg, 0.46 mmol), tris(dibenzylideneacetone)dipalladium (0) (3 mg, 0.0033 mmol), rac-2-2′-bis(diphenyl-phosphino)-1,1′-binaphthyl (3.1 mg, 0.005 mmol) was purged with nitrogen for 30 min, followed by the addition of anhydrous toluene (1.5 mL). The resulting light-brown solution was heated to 95° C. for 17. The mixture was brought to room temperature and partitioned between ethyl acetate and saturated NH4Cl. The organic phase was separated, washed with saturated NH4Cl, brine, dried over MgSO4 and chromatographed on silica gel using 3:1 hexanes:ethyl acetate to afford the title compound as a yellow oil. MS m/z: 291 (M+1).

Aufarbeitung

  1. customwas purged with nitrogen for 30 min
  2. additionfollowed by the addition of anhydrous toluene (1.5 mL)
  3. customwas brought to room temperature
  4. custompartitioned between ethyl acetate and saturated NH4Cl
  5. customThe organic phase was separated
  6. washwashed with saturated NH4Cl, brine
  7. dry with materialdried over MgSO4
  8. customchromatographed on silica gel using 3:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c4a24d4cfc06411988f71176d484cdb7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163766B2

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