Sodium Carbonate → Methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate

HRID 1259177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1259177
C(O[C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][C:10]=1B(O)O)=O)(C)(C)C.ClC1N=C(CCC2C=CC=CC=2)C=CC=1C#[N:26].Cl[C:40]1[C:41](C#N)=[N:42][CH:43]=[C:44](/[CH:46]=[CH:47]/[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:45]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CCOC(C)=O.O>[NH2:26][C:6]1[C:41]2[N:42]=[CH:43][C:44]([CH2:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:45][C:40]=2[C:10]2[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=2[N:8]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 668752372-(Tert-butoxycarbonylamino)-4-(methoxycarbonyl)phenylboronic acidHCID 66875239(E)-3-chloro-5-styrylpicolinonitrileHCID 856827592-Chloro-6-phenethylnicotinonitrile

Produkt 1

HCID 66874950Methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2-(tert-butoxycarbonylamino)-4-(methoxycarbonyl) phenylboronic acid (from Example 85/Step1) (1.0 eq.) and 2-chloro-6-phenethylnicotinonitrile (prepared from (E)-3-chloro-5-styrylpicolinonitrile (from Example 32/Step 1) following the procedure described in Example 114/Step3) (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (2.0 eq.) in toluene/ethanol (2:1, 0.03 M) was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and water. The two phases were separated, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-60% EtOAc/Hexanes to give methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-3aeb667e4f0347309063d5e494a64cf2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466167B2

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