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ChemicalBook CAS DataBase List ethyl 5-bromo-2-methyl-1H-indole-3-carboxylate
1245933-87-2

ethyl 5-bromo-2-methyl-1H-indole-3-carboxylate synthesis

3synthesis methods
66416-72-6 Synthesis
4-BROMO-2-IODOANILINE

66416-72-6
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$6.00/250mg

ethyl 5-bromo-2-methyl-1H-indole-3-carboxylate

1245933-87-2
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Yield:1245933-87-2 90%

Reaction Conditions:

with copper(l) iodide;caesium carbonate;1,1'-bi-2-naphthol in dimethyl sulfoxide at 50;

Steps:

12 Scheme 13.5

To a mixture of 4-Bromo-2-iodoaniline (1.38 g, 4.6 mmol) ethyl acetoacetate (0.67 g, 5.1 mmol), Cul (0.1 g, 0.52 mmol), and BINOL (0.2 g, 0.70 mmol) was added Cs2C03 (1.5 g, 4.60 mmol) in DMSO. After addition, the reaction mixture was heated at 50°C for overnight. After reaction was completed, the reaction mixture was diluted with Sat. NH4CI and EtOAc. The organic layer was washed with brine and dried over MgS04 to afford Compound 106 (ethyl 5-bromo-2-methyl-lH-indole-3-carboxylate) (1.17 g, 4.15 mmol, yield 90%). The product was used in next step without further purification.

References:

WO2019/108943,2019,A1 Location in patent:Paragraph 0280; 0322; 0323