Acetic Acid → 2-Bromo-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 1888471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888471
[BH4-].[Na+].Br.[Br:4][C:5]1[S:13][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1.[C:14](O)(=O)[CH3:15]>O1CCCC1>[Br:4][C:5]1[S:13][C:8]2[CH2:9][N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][C:7]=2[CH:6]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 670276802-bromo-4H,5H,6H,7H-thieno(2,3-c)pyridine hydrobromide

Produkt 1

HCID 582664752-Bromo-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium borohydride (146 mg, 3.85 mmol) was added to cooled (0° C.) a suspension of 2-bromo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide (230 mg, 0.77 mmol) in acetic acid (1.5 mL) and tetrahydrofuran (2.8 mL). On complete addition the mixture was heated to 60° C. for 3 h. The mixture was allowed to cool to ambient temperature then partitioned between ethyl acetate and water. The pH of the aqueous phase was adjusted to 10 by the addition of 3N sodium hydroxide solution and the layers separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to give the title compound as a yellow oil (181 mg, 96%). 1H NMR (DMSO-D6, 300 MHz): 6.93 (s, 1H), 3.50-3.47 (m, 2H), 3.66-2.46 (m, 6H), 1.05 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=1.79 min, M+H+=246/248.

Aufarbeitung

  1. additionOn complete addition the mixture
  2. temperaturewas heated to 60° C. for 3 h
  3. temperatureto cool to ambient temperature
  4. customthen partitioned between ethyl acetate and water
  5. additionThe pH of the aqueous phase was adjusted to 10 by the addition of 3N sodium hydroxide solution
  6. customthe layers separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-18c40b3c753b439c8187cef7429f26d2
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501765B2

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