Potassium Phosphate, Tribasic → tert-butyl ((2S)-1-((2-(5-(cyclopropylmethoxy)pyridin-2-yl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamate

HRID 2277155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277155
[O:1]1[C:5]2[CH:6]=[C:7]([O:10][CH2:11][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)=[CH:25][N:24]=1.C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN1CCCC1=O>[CH:31]1([CH2:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([C:2]3[O:1][C:5]4[CH:6]=[C:7]([O:10][CH2:11][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:8]=[CH:9][C:4]=4[N:3]=3)=[N:24][CH:25]=2)[CH2:32][CH2:33]1

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 578217962-Bromo-5-(cyclopropylmethoxy)pyridineHCID 86731209HCID 86731209, Verbindung

Produkt 1

HCID 86731208tert-butyl ((2S)-1-((2-(5-(cyclopropylmethoxy)pyridin-2-yl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)carbamateAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of tert-butyl ((2S)-1-(1,3-benzoxazol-6-yloxy)propan-2-yl)carbamate (516 mg), 2-bromo-5-(cyclopropylmethoxy)pyridine (604 mg), palladium(II) acetate (19.8 mg), butyldi(1-adamantyl)phosphine (63.3 mg), tripotassium phosphate (749 mg) and N-methylpyrrolidone (7 mL) was stirred at 125° C. for 15 hr under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (369 mg).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-554c111a0084499bb69015d27a3bcb54
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133129B2

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