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Sodium Carbonate → 4-(3-Fluorobenzyl)-N-(2-(5-phenyl-1H-indol-3-yl)ethyl)benzamide

HRID 1777680
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1777680
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][NH:22][C:23](=[O:38])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[F:37][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([NH:22][CH2:21][CH2:20][C:14]2[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:12]=3)[NH:16][CH:15]=2)=[O:38])=[CH:25][CH:26]=1
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Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86699393HCID 86699393, Verbindung

Produkt 1

HCID 679745944-(3-Fluorobenzyl)-N-(2-(5-phenyl-1H-indol-3-yl)ethyl)benzamideAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of benzeneboronic acid (0.024 g; 0.195 mmol), N-(2-(5-bromo-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide (0.080 g; 0.177 mmol), tetrakis(triphenylphosphine)palladium(0) (0.020; 0.017 mmol) and sodium carbonate (0.038 g; 0.355 mmol) in a mixture of DME (3 mL) and water (1 mL) was irradiated in the microwave oven at 130° C. for 20 minutes. The resulting solution was partitioned between water and ethyl acetate and the organic layer was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) and by preparative HPLC (method 2) to afford 0.013 g (16%) of the title compound as a white solid.

Aufarbeitung

  1. customwas irradiated in the microwave oven at 130° C. for 20 minutes
  2. customThe resulting solution was partitioned between water and ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) and by preparative HPLC (method 2)

Quellen und Nachweise

ORD-Eintrag
ord-63d23e0697644a75af3f69fa7a086cb2
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266832B2

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