Imidazole → 3-Cyano-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-4-carboxylic acid amide

HRID 2275229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275229
Br[C:2]1[C:3]([C:31]#[N:32])=[CH:4][CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[C:11]([CH3:16])([CH3:15])[C:10]3[CH:17]=[C:18]([O:21][CH2:22][C@H:23]4[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]4)[CH:19]=[CH:20][C:9]=3[C:8](=[O:30])[C:7]2=1.[NH:33]1[CH:37]=CN=C1.[OH2:38]>C(N)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:31]([C:3]1[C:2]([C:37]([NH2:33])=[O:38])=[C:14]2[C:6]([C:7]3[C:8](=[O:30])[C:9]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]5[CH2:27][O:26][C:25]([CH3:28])([CH3:29])[O:24]5)=[CH:17][C:10]=4[C:11]([CH3:16])([CH3:15])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)#[N:32]

Komponenten

7

Edukt 3

HCID 795ImidazoleHCID 962WaterHCID 668348924-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Produkt 1

HCID 668351393-Cyano-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-4-carboxylic acid amideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 713FormamideLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

Under nitrogen atmosphere, 4-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound U8-1, 30.0 mg, 60.56 mmol), palladium acetate (1.36 mg, 6.056 mmol), 1,1′-bis(diphenylphosphino)ferrocene (3.36 mg, 6.056 mmol), imidazole (4.12 mg, 60.56 mmol) and tert-potassium butoxy (10.2 mg, 90.84 mmol) were dissolved in formamide (3.00 mL) and the mixture was stirred at 180° C. for 5 min under irradiation with microwave. The reaction solution was poured into water, extracted with ethyl acetate, washed with water and saturated brine, dried over sodium sulfate, and then filtered. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (methanol/dichloromethane) to obtain the target compound (7.6 mg, 27%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-ab1528e3fe2c4a76a62c4443e9c85800
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126931B2

Notizen zur Reaktion

Wird geladen…