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ChemicalBook CAS DataBase List 6-Bromo-1H-indol-4-amine

6-Bromo-1H-indol-4-amine synthesis

4synthesis methods
-

Yield:350800-81-6 36%

Reaction Conditions:

with hydrogenchloride;titanium(III) chloride in water at 25; for 16 h;

Steps:

17.2 Step 2: 6-bromo-lH-indol-4-amine

The title compound from step 1 (3 g, 9.49 mmol) was treated with T1CI3 (7.32 g, 47.45 mmol) in a HCl solution (61.20 g, 167.86 mmol). The reaction mixture was stirred at 25 °C for 16 hr. It was then poured over 2 N aqueous NaOH (150 mL) and extracted with EtOAc (150 mL). The organic phase was dried, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (PE to PE/EA=5/1) to give the title compound (2 g, 36%) as a gray solid. H NMR (CDC13, 400 MHz) δ 8.10 (br s, 1 H ), 7.09-7.08 (m, 1 H), 7.02 (d, J = 1.4 Hz, 1 H), 6.54 (d, J = 1.4 Hz, 1 H), 6.44-6.43 (m, 1 H), 3.98 (br s, 2H).

References:

WO2016/168682,2016,A2 Location in patent:Paragraph 0256

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