Sodium Carbonate → 1-(4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenyl)ethanone

HRID 340376

Reaktionsgleichung

Reaktionsgleichung von HRID 340376
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12](Cl)[C:13]([C:16]#[N:17])=[N:14][CH:15]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:21][C:22]1[CH:23]=[CH:24][C:25](B2OC(C)(C)C(C)(C)O2)=[C:26]([NH:28]C(=O)OC(C)(C)C)[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(O)C.O>[NH2:17][C:16]1[C:13]2[N:14]=[CH:15][C:10]([CH2:9][CH2:8][C:7]3[CH:19]=[CH:20][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=3)=[CH:11][C:12]=2[C:25]2[CH:24]=[CH:23][C:22]([CH3:21])=[CH:27][C:26]=2[N:28]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 46737997tert-Butyl (5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 66892252HCID 66892252, Verbindung

Produkt 1

HCID 582136151-(4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 19096565Water ethanolLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-(4-acetylphenethyl)-3-chloropicolinonitrile (from the previous step) (1 eq) and tert-butyl 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (10 mol %), and 2N aqueous sodium carbonate solution (2.0 eq.) in toluene/ethanol (1:1, 0.09 M) was heated under microwave condition using a BIOTAGE INITIATOR 2.0 at 150° C. for 20 minutes. After cooling to ambient temperature, the reaction mixture was diluted with ethanol/water. The insoluble solids were filtered off, and the filtrate was concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 1-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)phenyl)ethanone as a yellow solid. 1H NMR (Methanol-d4) TFA Salt: δ 8.69 (d, 2H), 8.30 (d, 1H), 7.80 (d, 2H), 7.38 (s, 1H), 7.36 (d, 1H), 7.28 (d, 2H), 3.25 (t, 2H), 3.13 (t, 2H), 2.47 (s, 3H), 2.45 (s, 3H). LRMS [M+H]=356.2

Aufarbeitung

  1. customat 150° C.
  2. customfor 20 minutes
  3. filtrationThe insoluble solids were filtered off
  4. concentrationthe filtrate was concentrated en vacuo
  5. customto obtain a crude residue
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-634c005fba73496cb185d3087f17587b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895577B2

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