Réaction #66078

Équation de réaction

(2-Bromo-4-fluorophenyl)hydrazine hydrochloride

product

1-azabicyclo[3.2.2]nonan-4-one

→

title compound

7-bromo-9-fluoro-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Solvants

HCl acetic acid

Conditions de réaction

Traitement

1. 1
   Températureto cool
2. 2
   Concentrationconcentrated
3. 3
   AutreThe product was triturated with acetonitrile
4. 4
   Autreisolated by filtration
5. 5
   Lavagewashing with additional acetonitrile (2×10 mL)
6. 6
   AutreThe solid was partitioned between 1.0 M NaOH (50 mL) and CHCl3 (3×50 mL)
7. 7
   SéchageThe combined organic extracts were dried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

Mode opératoire

(2-Bromo-4-fluorophenyl)hydrazine hydrochloride (1.14 g, 4.72 mmol; Enamine) was suspended in HCl-acetic acid (1.0 M, 25 mL; Aldrich). The product of Example 1A (684 mg, 4.91 mmol) was added and the reaction was heated to 80° C. for 5 hours. The reaction was then allowed to cool and then concentrated. The product was triturated with acetonitrile and isolated by filtration, washing with additional acetonitrile (2×10 mL). The solid was partitioned between 1.0 M NaOH (50 mL) and CHCl3 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.05-2.11 (m, 4H), 3.01-3.14 (m, 3H), 3.19-3.26 (m, 2H), 4.17 (s, 2H), 6.96-7.04 (m, 2H); MS (DCI/NH3) m/z 309/311 (M+H)+. Anal. Calcd. for C14H14BrFN2: C, 54.39; H, 4.56; N, 9.06. Found: C, 54.04; H, 4.28; N, 8.90.

Source