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4-(Dimethylamino)phenylboronic acid → Ethyl N-(3,4-dichlorobenzyl)-5-(4-[N,N-dimethylamino]phenyl)indole-2-carboxylate

HRID 2305583
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2305583
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2.[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[CH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:30]3[CH:31]=[CH:32][C:27]([N:26]([CH3:36])[CH3:25])=[CH:28][CH:29]=3)=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 27343444-(Dimethylamino)phenylboronic acidHCID 22310916Ethyl 5-bromo-N-(3,4dichlorobenzyl)indole-2-carboxylate

Produkt 1

HCID 18433334Ethyl N-(3,4-dichlorobenzyl)-5-(4-[N,N-dimethylamino]phenyl)indole-2-carboxylateAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178527695HCID 178527695, VerbindungKatalysator
HCID 21863594
Toluene ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 5-bromo-N-(3,4dichlorobenzyl)indole-2-carboxylate (0.3 g), 4-dimethylaminobenzene boronic acid (0.13 g) and tetrakis triphenylphosphine-palladium(0) (20 mg) were dissolved in degassed toluene/ethanol/2M potassium carbonate (2:2:1) under argon and warmed at 80° C. for 16 hours. The reaction was then cooled to room temperature and partitioned between 2M HCl and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using i-hexane-15% ethyl acetate as eluent to give the desired end product as a pale brown solid (0.25 g, 76%); NMR δ(CDCl3) 1.38 (t, 3H), 2.98 (s, 6H), 4.38 (q, 2H), 5.78 (s, 2H), 6.80-7.80 (m, 11H); M/z (+) 467 (M+), 319, 280, 239.

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. custompartitioned between 2M HCl and ethyl acetate
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9c5c74a6d52a4355b7fb0e1ba884fbf4
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06441004B1

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