Hydrochloric Acid → 5-Formyl-1H-indole-3-carbonitrile

HRID 2250261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250261
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]#[N:12].[H-].[Na+].C([Li])(CC)C.C1CCCCC1.Cl.[C:27](=O)(O)[O-:28].[Na+]>CN(C)C=O.O1CCCC1>[CH:27]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]#[N:12])=[O:28]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 8078CyclohexaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 36233545-Bromo-3-cyanoindoleHCID 178418400CID 53628100

Produkt 1

HCID 211022025-Formyl-1H-indole-3-carbonitrileAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Bromo-1H-indole-3-carbonitrile (4.25 g, 19.23 mmol) and sodium hydride (0.51 g, 21.2 mmol) were weighed into a flame-dried round-bottom flask containing a magnetic stir bar. Under a nitrogen atmosphere at room temperature, dry tetrahydrofuran (24 mL) was added. The mixture was stirred at room temperature for 15 min, during which time it became homogeneous. The stirred mixture was cooled to −78° C. and a solution of sec-butyllithium in cyclohexane (1.4M, 30.2 mL, 2.2 equiv) was added over several minutes. After 1 h at −78° C., dimethylformamide (6.0 mL) was slowly added and the mixture allowed to warm to room temperature overnight. The solution was cooled to 0° C. and carefully treated with 1 N hydrochloric acid (45 mL). After a few minutes, solid sodium bicarbonate was added until a pH of 9-10 was attained. The two layers were separated and the aqueous phase washed twice with ethyl acetate. The combined organic layers were washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography gave 2.4 g (72%) of pure material. LC/MS: tR=0.99 min, 171.07 (MH)+.

Aufarbeitung

  1. additioncontaining a magnetic stir bar
  2. temperatureThe stirred mixture was cooled to −78° C.
  3. waitAfter 1 h at −78° C.
  4. temperatureto warm to room temperature overnight
  5. temperatureThe solution was cooled to 0° C.
  6. waitAfter a few minutes
  7. customThe two layers were separated
  8. washthe aqueous phase washed twice with ethyl acetate
  9. washThe combined organic layers were washed with water (2×), brine (2×)
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1a061c990fdf415aba0daac2a36d7db9
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314883B2

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