Nitrogen → tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

HRID 2173287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173287
Br[C:2]1[C:3]([O:26][CH3:27])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[O:7][CH2:6][CH2:5]2.N#N.[CH3:30][N:31](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[C:30]([C:2]1[C:3]([O:26][CH3:27])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]1)[O:7][CH2:6][CH2:5]2)#[N:31]

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 68433391tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

Produkt 1

HCID 67517697tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

To a solution of tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate (50 mg, 0.11 mmol), Pd(PPh3)4 (20 mg) and Zn(CN)2 (26 mg, 0.23 mmol) in 5 mL of anhydrous DMF was to 110° C. at N2 atmosphere overnight. The reaction was cooled to room temperature, extracted by EtOAc, washed by water then by brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate.

Aufarbeitung

  1. extractionextracted by EtOAc
  2. washwashed by water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with prep-TLC

Quellen und Nachweise

ORD-Eintrag
ord-89986f29258e4ca5b6deff20df97e613
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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