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Dimethylformamide → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-cyano-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 2353876
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2353876
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([C:30](=[O:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C:9]2[CH:33]=[CH:34][C:35](Br)=[CH:36][C:8]1=2)=[O:6])([CH3:3])[CH3:2].[CH3:38][N:39](C)C=O>C(OCC)(=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:30]([N:14]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1)[CH:10]1[CH2:11][CH2:12][CH2:13][N:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[C:8]2[CH:36]=[C:35]([C:38]#[N:39])[CH:34]=[CH:33][C:9]1=2)(=[O:32])[CH3:31]
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Komponenten

7

Edukt 2

HCID 6228DimethylformamideHCID 59003154Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Produkt 1

HCID 86616065Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-cyano-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysator2×
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Purge with nitrogen, a solution of isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.074 g, 0.124 mmol) and zinc cyamide (0.014 g, 0.124 mmol) in N,N-dimethylformamide (2 mL) in a 10 mL microwave vial. Add tetrakis(triphenylphosphine)palladium (0) (0.0043 g, 0.0037 mmol) and irradiate the mixture at 175° C. for 0.5 h (60-80 Watts). Add a second portion of zinc cyamide (0.014 g, 0.124 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.0043 g, 0.0037 mmol) and continue irradiating for 8 min. Cool the mixture to room temperature and dilute with ethyl acetate (35 mL) and wash with water (3×25 mL) and brine (25 mL each), then dry the organic layer over sodium sulfate, filter and remove the solvent under reduced pressure. Purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound as a crushable white foam (0.034 g, 51%): ESI MS 542 (M+H).

Aufarbeitung

  1. customPurge with nitrogen
  2. customcontinue irradiating for 8 min
  3. washwash with water (3×25 mL) and brine (25 mL each)
  4. dry with materialdry the organic layer over sodium sulfate
  5. filtrationfilter
  6. customremove the solvent under reduced pressure
  7. customPurify the residue
  8. washeluting with hexanes/ethyl acetate (60:40)

Quellen und Nachweise

ORD-Eintrag
ord-464f9ca239094c4d95223b791f0c87fe
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07749992B2

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