Tricyclohexylphosphine → HCID 67959399, Verbindung

HRID 1404973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404973
Br[C:2]1[C:11]2[O:10][CH:9]([CH3:12])[CH2:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][C:5]=2[S:4][CH:3]=1.[CH:20]1(B(O)O)[CH2:22][CH2:21]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CC(C)([O-])C.[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:20]1([C:2]2[C:11]3[O:10][CH:9]([CH3:12])[CH2:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][C:5]=3[S:4][CH:3]=2)[CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 23665647Potassium tert-butoxideHCID 67958981tert-butyl 8-bromo-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate

Produkt 1

HCID 67959399HCID 67959399, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of tert-butyl 8-bromo-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (348 mg) obtained in Example 6, steps 1-6, cyclopropylboronic acid (129 mg), palladium acetate (11.2 mg), tricyclohexylphosphine (28 mg), potassium tert-butoxide (337 mg) and toluene (5 mL) was stirred at 80° C. for 16 hr under an argon atmosphere. The reaction solution was cooled to room temperature, and filtered through celite. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane) to give the title compound (266 mg, 86%) as a pale-yellow oil.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered through celite
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4fdba88a79fd4f849a133999b662862b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916549B2

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