Potassium Carbonate → HCID 67418952, Verbindung

HRID 625947

Reaktionsgleichung

Reaktionsgleichung von HRID 625947
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([C:24]2[CH:28]=[CH:27][NH:26][N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].CNC1CCCCC1NC>O1CCOCC1.CCOC(C)=O.[Cu]I>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([N:26]2[CH:27]=[CH:28][C:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:25]2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine2×HCID 674178603-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-oneHCID 178420101HCID 178420101, Verbindung

Produkt 1

HCID 67418952HCID 67418952, VerbindungAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator2×HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-(Benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (50 mg, 0.170 mmol), 3-phenyl-1H-pyrazole (29 mg, 0.201 mmol), K2CO3 (47.0 mg, 0.340 mmol), CuI (2 mg, 10.50 μmol), and N,N′-dimethyl-1,2-cyclohexanediamine (6 μl 0.038 mmol) were combined in 1,4-dioxane (0.5 mL) in a screw cap vial. The vial was sealed then heated to 110° C. After stirring overnight the mixture was cooled to RT. CuI (2 mg) and N,N′-dimethyl-1,2-cyclohexanediamine (6 uL) were added and heating continued at 110° C. After stirring overnight the mixture was cooled to RT and diluted with EtOAc. The resulting mixture was filtered and concentrated. The crude material was purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-70% CH3CN/water over 20 min at 20 mL/min) to give the title compound (33 mg, 54%) as an amber film. 1H NMR (500 MHz, CDCl3): δ 7.85 (d, J=7.7 Hz, 2 H); 7.61 (d, J=2.5 Hz, 1 H); 7.50-7.32 (m, 9 H); 7.12 (d, J=2.6 Hz, 1 H); 6.73 (d, J=2.5 Hz, 1 H); 5.21 (s, 2 H); 3.68 (s, 3 H). LC/MS (M+H)+ 358.

Aufarbeitung

  1. customcap vial
  2. customThe vial was sealed
  3. temperaturewas cooled to RT
  4. temperatureheating
  5. customcontinued at 110° C
  6. stirringAfter stirring overnight the mixture
  7. temperaturewas cooled to RT
  8. filtrationThe resulting mixture was filtered
  9. concentrationconcentrated
  10. customThe crude material was purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-70% CH3CN/water over 20 min at 20 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-7c0eca7314864ade95dd0c29aad64760
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309199B2

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