Reaktion #61625

Reaktionsgleichung

hydrazine hydrate

Compound 28

1,5-Dihydro-3-phenyl-[1,2]diazepino[4,5,6-cd]-indol-6-one

methyl indole-4-carboxylate

p-trifluoromethylbenzoyl chloride

aluminum chloride

→

4-trifluoromethylphenyl-[1,2]diazepino[4,5,6-cd]indol-6-one

Lösungsmittel

MeOH

HCl

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched at 0° C. with w M NaOAc
2. 2
   SonstigeThe product was isolated by extraction with CH2Cl2
3. 3
   Sonstigerecrystallized (CH2Cl2/hexanes)

Vorschrift

In a manner similar to that described for Compound 28, a solution of methyl indole-4-carboxylate (250 mg, 1.43 mmol) in dichloroethane (3 mL) was treated with p-trifluoromethylbenzoyl chloride (445 mg, 2.14 mmol) and aluminum chloride (572 mg). The intermediate ketone (95 mg, 0.27 mmol) in MeOH (3 mL) and conc. HCl (0.05 mL) was treated, as described, with hydrazine hydrate (0.1 mL). The reaction was quenched at 0° C. with w M NaOAc and the aqueous layer was adjusted to pH=8 with 1 M NaOH. The product was isolated by extraction with CH2Cl2, and recrystallized (CH2Cl2/hexanes) to give 1,5-dihydro-3-(4-trifluoromethylphenyl-[1,2]diazepino[4,5,6-cd]indol-6-one, 30 mg (34%) as a yellow solid: 1H NMR (300 MHz, d6-DMSO) δ 7.24 (app br t, 1H), 7.29 (d, J=2.8 Hz, 2H), 7.60 (m, 2H), 7.82 (m, 4H), 10.57 (s, 1H), 12.01 (s, 1H). HRMS (FAB, Mna+) Calcd for C11H10N3Ona: 352.0674. Found: 352.0668.

Quelle