Ethanol → 2-(Methylamino)-2-oxoethyl 4-(5-{4-[(trifluoro-methyl)oxy]phenyl}-2-pyridyl)-1,4-diazepane-1-carboxylate

HRID 2246226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246226
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[O:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1>[F:23][C:24]([F:35])([F:36])[O:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[O:16])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 602095672-(Methylamino)-2-oxoethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylate

Produkt 1

HCID 592182162-(Methylamino)-2-oxoethyl 4-(5-{4-[(trifluoro-methyl)oxy]phenyl}-2-pyridyl)-1,4-diazepane-1-carboxylateAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

0.12 g (0.3 mmol) of 2-(methylamino)-2-oxoethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylate, prepared in step 11.3., 0.25 g (1.2 mmol) of 4-(trifluoromethoxy)-phenylboronic acid and 0.9 ml (1.8 mmol) of aqueous sodium carbonate solution (2M), suspended in 3.5 ml of toluene and 0.8 ml of ethanol are introduced into a Pyrex reactor. 0.07 g (0.06 mmol) of tetrakis-(triphenylphosphine)palladium is then added and, after sealing the reactor, it is maintained at 150° C. for 15 minutes under microwave irradiation. The organic phase is recovered after separation of the phases by settling, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 30/70/5 mixture of ethyl acetate, cyclohexane and methanol. After crystallization from diisopropyl ether, 0.078 g of product is obtained in the form of a white solid.

Aufarbeitung

  1. customThe organic phase is recovered
  2. customafter separation of the phases
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue thus obtained
  5. customis purified by chromatography on silica gel
  6. washeluting with a 30/70/5 mixture of ethyl acetate, cyclohexane and methanol
  7. customAfter crystallization from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b83348b615f14da28ef87f546705988d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687503B2

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