tert-Butyl piperazine-1-carboxylate → HCID 67125779, Verbindung

HRID 2042408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042408
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([CH3:11])=[CH:4][N:3]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:11][C:5]1[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[N:3][CH:4]=1

Komponenten

8

Edukt 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 14372148HCID 14372148, VerbindungHCID 23676156Sodium t-butoxide

Produkt 1

HCID 67125779HCID 67125779, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A stirred mixture of commercially available 4-chloro-7-methyl-furo[3,2-c]pyridine (2.5 g, 14.9 mmol), tert-butyl piperazine-1-carboxylate (3.33 g, 17.9 mmol), sodium tert.-butoxide (2.01 g, 20.9 mmol), palladium(II) acetate (335 mg, 1.49 mmol) and 2-(di-tert.-butylphosphino) biphenyl (445 mg, 1.49 mmol) in toluene (33.0 ml) was heated for 16 h at 100° C. The mixture was cooled and water (10 ml) was added. The mixture was extracted with ethylacetate (2×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude product (5.9 g) was further purified by flash chromatography on silica gel (10% to 100% ethyl acetate in heptane) to yield tert-butyl 4-(7-methyl-furo[3,2-c]pyridin-4-yl)-piperazine-1-carboxylate as a yellow solid (2.35 g, 50%), MS (ISP) m/z=318.3 [(M+H)+], mp 108.5° C.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethylacetate (2×20 ml)
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product (5.9 g) was further purified by flash chromatography on silica gel (10% to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-44b73e40746d45a6b0b319d5d5cacc78
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586579B2

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