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

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ethyl 3-methyl-1H-indole-5-carboxylate Basic information
Product Name:ethyl 3-methyl-1H-indole-5-carboxylate
Synonyms:ethyl 3-methyl-1H-indole-5-carboxylate;3-Methyl-5-carbethoxyindole;1H-Indole-5-carboxylic acid, 3-methyl-, ethyl ester
CAS:73396-90-4
MF:C12H13NO2
MW:203.24
EINECS:
Product Categories:
Mol File:73396-90-4.mol
ethyl 3-methyl-1H-indole-5-carboxylate Structure
ethyl 3-methyl-1H-indole-5-carboxylate Chemical Properties
Boiling point 353.5±22.0 °C(Predicted)
density 1.177±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. Sealed in dry,Room Temperature
pka16.39±0.30(Predicted)
Safety Information
MSDS Information
ethyl 3-methyl-1H-indole-5-carboxylate Usage And Synthesis
Synthesis
Palladium (II) Acetate

3375-31-3

Benzoic acid, 3-bromo-4-(2-propen-1-ylamino)-, ethyl ester

73396-89-1

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

73396-90-4

(1) Synthesis of 5-ethoxy-3-methylindole: To a solution of 2-bromo-4-ethoxy-N-allyl aniline (650 mg, 2.29 mmol) in acetonitrile (10 mL) was added sequentially tetrakis(triphenylphosphine)palladium(0) (132 mg, 0.114 mmol), palladium(II) acetate (25.7 mg, 0.114 mmol) and triethylamine (0.413 mL, 2.98 mmol). The reaction mixture was stirred in a sealed tube at 100 °C overnight. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane = 1:2) to afford ethyl 3-methyl-1H-indole-5-carboxylate (340 mg, 73% yield). NMR hydrogen spectrum (CDCl3, method a): δ 1.43 (3H, t, J = 7.2 Hz), 2.37 (3H, s), 4.41 (2H, q, J = 7.2 Hz), 7.03 (1H, s), 7.34 (1H, d, J = 8.6 Hz), 7.91 (1H, dd, J = 1.3, 8.6 Hz), 8.08 (1H brs), 8.36 (1H, s).

References[1] Patent: US6586630, 2003, B1
ethyl 3-methyl-1H-indole-5-carboxylate Preparation Products And Raw materials
Raw materialsPalladium (II) Acetate-->Benzoic acid, 3-bromo-4-(2-propen-1-ylamino)-, ethyl ester-->Acetonitrile-->Triethanolamine
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