Potassium Phosphate, Tribasic → HCID 59548528, Verbindung

HRID 1879682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879682
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:13]=1.[CH:14]1(B(O)O)[CH2:16][CH2:15]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:14]1([C:2]2[CH:3]=[CH:4][C:5]3[C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]=3[CH:13]=2)[CH2:16][CH2:15]1

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 595485548-Bromo-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one

Produkt 1

HCID 59548528HCID 59548528, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 8-Bromo-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (1.02 g, 4.23 mmol, 1 eq), cyclopropylboronic acid (480 mg, 5.5 mmol, 1.3 eq), tricyclohexylphosphine (121 mg, 0.42 mmol, 0.1 eq), Pd(OAc)2 (48 mg, 0.211 mmol, 0.05 eq), K3PO4 (3.2 g, 14.8 mmol, 3.5 eq) in Toluene (40 mL), water (4 mL), dioxane (10 mL), was degassed with argon and heated to 110 C for 15 hours. The reaction was cooled, diluted with ethyl acetate, washed sat. aq. Sodium bicarbonate solution, brine, and dried over mgso4, filtered, concentrated in vacuo and purified with flash chromatography on a silica gel column eluting with 50% ethyl acetate in hexanes to give 650 mg 8-Cyclopropyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one, 76%.

Aufarbeitung

  1. customwas degassed with argon
  2. temperatureheated to 110 C for 15 hours
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed sat. aq. Sodium bicarbonate solution, brine
  6. customdried over mgso4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified with flash chromatography on a silica gel column
  10. washeluting with 50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b1f7acfe5cdb447b9735ff1f37aeb066
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318719B2

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