Triethylamine → 3-(9-(biphenyl-4-ylmethyl)-9H-carbazol-3-yl)acrylic acid tert-butyl ester

HRID 1637652

Reaktionsgleichung

Br[C:2]1[C:14]2N[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4]C=1.[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:20]([O:19][C:15](=[O:18])[CH:16]=[CH:17][C:10]1[CH:11]=[CH:25][C:24]2[N:26]([CH2:29][C:30]3[CH:4]=[CH:5][C:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[CH:14][CH:2]=3)[C:27]3[C:7]([C:8]=2[CH:9]=1)=[CH:6][CH:5]=[CH:4][CH:28]=3)([CH3:23])([CH3:22])[CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of the above bromo-carbazole (7.15 g, 18 mmol), tert-butyl acrylate (3.01 g, 23.3 mmol), palladium acetate (40 mg, 0.2 mmol), tri-o-tolylphosphine (220 mg, 0.7 mmol) and triethylamine (10 ml) in an screw cap ampoule was heated at 100° C. for 20 h. The cooled reaction mixture was diluted with ethyl acetate (75 ml), washed with water (3×20 ml), dried (MgSO4), filtered and evaporated in vacuo. The residue (9.6 g) was purified by column chromatography on silicagel (600 ml) using toluene as eluent which afforded 4.92 g (60%) of 3-(9-(biphenyl-4-ylmethyl)-9H-carbazol-3-yl)acrylic acid tert-butyl ester as a solid.

Aufarbeitung

customcap ampoule
customThe cooled reaction mixture
washwashed with water (3×20 ml)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated in vacuo
customThe residue (9.6 g) was purified by column chromatography on silicagel (600 ml)

Quellen und Nachweise

ORD-Eintrag: ord-8ea4cdf845754ffcba27bb389534a74e
Quelldatensatz: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06043247

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