Potassium Carbonate → Ethyl 7-(2-(pyridin-4-yl)-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 406228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406228
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:9][CH2:10][CH2:11][C:5]2=[N:4][C:3]=1[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.B(O)(O)[C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:26]1[CH:27]=[CH:28][C:23]([C:3]2[N:4]=[C:5]3[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:6]3=[N:7][C:2]=2[C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 86681855Ethyl 7-(3-chloro-2-(pyridin-4-yl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Produkt 1

HCID 66666060Ethyl 7-(2-(pyridin-4-yl)-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of ethyl 7-(3-chloro-2-(pyridin-4-yl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 3) (58 mg, 0.144 mmol), p-tolylboronic acid (39.1 mg, 0.288 mmol) and potassium carbonate (59.7 mg, 0.432 mmol) in dioxane (2 ml) was degassed by bubbling nitrogen through (×3). Pd(Ph3P)4 (33.3 mg, 0.029 mmol) was added and the mixture was degassed by bubbling nitrogen through (×3). The mixture was heated at 150° C. for 2 hours using microwave irradiation. The mixture was diluted with water and extracted with EtOAc (×2). The combined extracts were washed with brine, dried (MgSO4) and evaporated under vacuum. The crude product was purified by chromatography on silica eluting with 50-100% EtOAc in iso-hexane followed by 5-10% THF in DCM. The fractions were evaporated under vacuum and the residue was purified by ion exchange using a Isolute SCX-2 cartridge, loading and washing with methanol and eluting with 2M NH3 in MeOH to afford the title compound;

Aufarbeitung

  1. customwas degassed
  2. customby bubbling nitrogen through (×3)
  3. customthe mixture was degassed
  4. customby bubbling nitrogen through (×3)
  5. custommicrowave irradiation
  6. additionThe mixture was diluted with water
  7. extractionextracted with EtOAc (×2)
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated under vacuum
  11. customThe crude product was purified by chromatography on silica eluting with 50-100% EtOAc in iso-hexane
  12. customThe fractions were evaporated under vacuum
  13. customthe residue was purified by ion exchange
  14. washwashing with methanol
  15. washeluting with 2M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-d0755594c8f7477c821cccadc6034727
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754085B2

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