Potassium Carbonate → {(1S,4S)-4-[2-(2-Methoxy-acetylamino)-pyridin-4-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-carbamic acid tert-butyl ester

HRID 2282376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282376
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](Cl)[CH:20]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][CH2:29][C:30]([NH2:32])=[O:31].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:32][C:30](=[O:31])[CH2:29][O:28][CH3:27])[CH:20]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 1400602-MethoxyacetamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86686964[(1S,4S)-4-(2-Chloro-pyridin-4-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 86686965{(1S,4S)-4-[2-(2-Methoxy-acetylamino)-pyridin-4-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-carbamic acid tert-butyl esterAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Intermediate 10b (562 mg, 1.50 mmol), 2-methoxyacetamide (334 mg, 3.75 mmol), Xantphos (173 mg, 0.30 mmol) and potassium carbonate (518 mg, 3.75 mmol) were suspended in 1,4-dioxane (20 mL), warmed, degassed, and placed under argon. To this mixture palladium acetate (34.0 mg, 0.15 mmol) was added. The mixture was degassed and then heated at reflux for 17 h. After cooling, the mixture was filtered through Celite, washing with DCM, and evaporated to a yellow gum. Purification by FCC, eluting with 0-100% ethyl acetate in cyclohexane, gave the title compound as a white foam (281 mg, 44%). LCMS (Method 3): Rt 3.27 min, m/z 450.2 [MNa+].

Aufarbeitung

  1. temperaturewarmed
  2. customdegassed
  3. customThe mixture was degassed
  4. temperatureheated
  5. temperatureat reflux for 17 h
  6. temperatureAfter cooling
  7. filtrationthe mixture was filtered through Celite
  8. washwashing with DCM
  9. customevaporated to a yellow gum
  10. customPurification by FCC
  11. washeluting with 0-100% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-8dbb80f7cfe74913b97687581e75d2ce
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139584B2

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