N,N,N-trimethylglycinium → 1-(2-bromo-ethyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246439

Reaktionsgleichung

Reaktionsgleichung von HRID 2246439
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]#[N:17])[C:13]3[N:18]=[CH:19][NH:20][C:12]=3[CH:11]=2)=[CH:6][C:5]=1[C:21]([F:24])([F:23])[F:22])[CH3:2].[Br:25][CH2:26][CH2:27]O.C[N+](CC(O)=O)(C)C>C1COCC1>[Br:25][CH2:26][CH2:27][N:20]1[C:12]2[CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:21]([F:23])([F:24])[F:22])[CH:6]=3)[N:15]=[C:14]([C:16]#[N:17])[C:13]=2[N:18]=[CH:19]1

Komponenten

5

Edukt 3

HCID 248N,N,N-trimethylglycinium2×HCID 108982-BromoethanolHCID 16662142HCID 16662142, Verbindung

Produkt 1

HCID 589381211-(2-bromo-ethyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-(4-Ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (300 mg, 0.90 mmol) was dissolved in THF (10 ml), 2-bromoethanol was added (225 mg, 1.80 mmol) followed by betaine (738 mg, 1.80 mmol), and the mixture was stirred at room temperature for 3 hours. A further 0.5 equivalents of betaine (0.45 mmol, 162 mg) was added and the mixture was stirred at room temperature for a further hour. Mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). Organics were dried and evaporated then flash chromatographed over silica (10 g Combiflash cartridge, DCM to 1% methanol in DCM) to afford a white solid which was mixture of N-1 and N-3 alkylated products. Mixture was flash chromatographed over silica (10 g Flashmaster cartridge, toluene to 20% ethyl acetate in toluene) to afford 130 mg of 1-(2-bromo-ethyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile as a white solid. 1H NMR (DMSO) δ 8.80 (s, 1H), 8.74 (s, 1H), 8.48-8.39 (m, 2H), 7.44 (d, 1H), 4.88 (t, 2H), 4.29 (q, 2H), 4.05 (t, 2H), 1.40 (t, 3H).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for a further hour
  2. customMixture was partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. customOrganics were dried
  4. customevaporated
  5. customflash chromatographed over silica (10 g Combiflash cartridge, DCM to 1% methanol in DCM)
  6. customto afford a white solid which
  7. additionmixture of N-1 and N-3 alkylated products
  8. customchromatographed over silica (10 g Flashmaster cartridge, toluene to 20% ethyl acetate in toluene)

Quellen und Nachweise

ORD-Eintrag
ord-a4fc108a3c0d45e2ad8cde02e32f1814
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687515B2

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