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Ethanol → 2-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 1259124
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259124
N1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[C:11][C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[C:19]3[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]3=[N:17][C:16]=4[NH2:27])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:30])C.[H][H]>[Pd].C(Cl)Cl>[O:30]1[C:9]2[CH:8]=[CH:7][C:6]([CH2:10][CH2:11][C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[C:19]3[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]3=[N:17][C:16]=4[NH2:27])=[CH:5][C:4]=2[CH2:3][CH2:2]1
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Komponenten

6

Edukt 3

HCID 702EthanolHCID 668930492-((1H-indol-5-yl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 442314112-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a round bottom flask was added 2-((1H-indol-5-yl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (from the previous step) (1 eq.) with a stirring bar. Ethanol and methylene chloride (1:2, 0.2 M) were added, followed by palladium in carbon (activated powder, wet, 10% on carbon, 0.1 eq.). The content were vacuumed followed by hydrogen flush for three times. The reaction mixture was stirred vigorously under hydrogen balloon at room temperature overnight. Afterwards the reaction mixture was filtered through a celite pad, and the celite pad was washed subsequently with methylene chloride and EtOAc until the filtrate had no UV absorption. Combined organic washes were concentrated. Flash chromatography (silica gel, 0-50% EtOAc in CH2Cl2) afforded the product 2-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (CDCl3): δ 8.54 (d, 1H), 8.34 (d, 1H), 8.28 (s, 1H), 7.99 (d, 1H), 7.64-7.56 (m, 1H), 7.50-7.35 (m, 1H), 7.24 (d, 1H), 7.12 (t, 1H), 7.08 (dd, 1H), 6.92 (dd, 1H), 6.41 (s, 1H), 6.01 (bs, 2H), 3.16-3.12 (m, 2H), 3.10-3.05 (m, 2H), 2.43 (s, 3H). LRMS [M+H]=353.2

Aufarbeitung

  1. customflush for three times
  2. filtrationAfterwards the reaction mixture was filtered through a celite pad
  3. washthe celite pad was washed subsequently with methylene chloride and EtOAc until the filtrate
  4. customno UV absorption
  5. concentrationCombined organic washes were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb69f8c363f5438fa3804f85f9cc695a
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466167B2

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