Diisopropylamine → 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide

HRID 2383515

Reaktionsgleichung

Reaktionsgleichung von HRID 2383515
Br[C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:25])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][O:22][C:23]=3[CH3:24])=[CH:15][CH:14]=2)[CH3:9])=[N:6][CH:7]=1.[CH:26](B1OC(C)(C)C(C)(C)O1)=[CH2:27].CC1C(P(C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)=CC(S([O-])(=O)=O)=C(C)C=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C>CC#N.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][C:23]1[O:22][N:21]=[CH:20][C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:11]([NH:10][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([CH:26]=[CH2:27])=[CH:7][N:6]=2)[CH3:9])=[O:25])=[CH:14][CH:15]=1

Komponenten

8

Edukt 4

HCID 7912DiisopropylamineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 11239198TxptsHCID 24765670N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide

Produkt 1

HCID 247655772-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 0.18 g (0.46 mmol) N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide in 0.50 ml CH3CN and 0.50 ml water was added 0.07 g (0.46 mmol) 2-vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.02 g (0.03 mmol) TXPTS, 0.003 g (0.01 mmol) Palladium (II) acetate, and 0.13 mL (0.92 mmol) diisopropylamine. After 20 min in the microwave at 120° C., the reaction mixture was cooled, extracted with CH2Cl2, and washed with brine. The organic layer was dried over NaSO4, filtered, and concentrated in vacuo. Purification by flash chromatography (1×14 cm silica gel, linear gradient 40-85% EtOAc:hexane) afforded 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide. Electrospray mass spec M+H=348.1.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (1×14 cm silica gel, linear gradient 40-85% EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e4b0222e8b4d430c91b7631aa6ff7374
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263627B2

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