4-Chloro-1H-pyrrolo[2,3-b]pyridine → 4-(4-Phenyl-1H-imidazol-1-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1524657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524657
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[C:11]1([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([C:17]2[N:18]=[CH:19][N:20]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[NH:8][CH:9]=[CH:10][C:3]=34)[CH:21]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

3

Edukt 2

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 178418822HCID 178418822, Verbindung

Produkt 1

HCID 177544094-(4-Phenyl-1H-imidazol-1-yl)-1H-pyrrolo[2,3-b]pyridineAusbeute 291 %

Versuchsvorschrift

A melt of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.00033 mol) in 4-phenyl-1H-imidazole (0.24 g, 0.0016 mol) was heated at 200° C. overnight. The reaction was partitioned between ethyl acetate and saturated NaHCO3, separated and the organic phase was washed with brine. The organic layer was then dried and evaporated to give 250 mg of an orange oil. The oil was chromatographed with 7% MeOH/DCM, 0.7% NH4OH, sample in solvent system. Collected 74 mg of the product as an orange glass. The glass was triturated with hot DCE (1.5 mL) to give 51 mg of a brown solid which was dried at 60° C. for 4 h to afford the desired product (50 mg, 59 yield).

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and saturated NaHCO3
  2. customseparated
  3. washthe organic phase was washed with brine
  4. customThe organic layer was then dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-183d4c9afafb44dda547e475e9f50ff1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079912B2

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