ChemicalBook CAS DataBase List 1-Methyl-6-chloro-1H-indole-2-carboxylic acid ethyl ester

1-Methyl-6-chloro-1H-indole-2-carboxylic acid ethyl ester synthesis

7synthesis methods

Product Name:1-Methyl-6-chloro-1H-indole-2-carboxylic acid ethyl ester
CAS Number:43142-81-0
Molecular formula:C12H12ClNO2
Molecular Weight:237.68

27034-51-1 Synthesis

6-Chloroindole-2-carboxylic acid ethyl ester

27034-51-1
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74-88-4
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1-Methyl-6-chloro-1H-indole-2-carboxylic acid ethyl ester

43142-81-0
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Yield:43142-81-0 100%

Reaction Conditions:

Stage #1: ethyl 6-chloro-1H-indole-2-carboxylatewith sodium hydride in N,N-dimethyl-formamide at 20; for 1 h;Inert atmosphere;
Stage #2: methyl iodide in N,N-dimethyl-formamide at 20; for 4 h;Inert atmosphere;

Steps:

Ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate (4)

To a suspension of sodium hydride (0.73 g, 29 mmol) in dry N,N-dimethylformamide(58 mL) was added 3 (6.1 g, 27.4 mmol) at room temperature and the reaction mixture was stirred under argon for 1 h before addition of methyl iodide (1.82 mL, 29 mmol).The reaction mixture was stirred at room temperature for 4 h and evaporated to give a residue which was redistributed in dichloromethane(200 mL) and water (300 mL). The organic layer was separated and washed twice with water (2 200 mL) before beingdried (Na2SO4). Evaporation followed by crystallization in ethanol gave 4 as beige crystals (6.5 g, quantitative). Rf (heptane/ethyl acetate,7/3): 0.52. Mp: 75-76 C. 1H NMR (CDCl3) d 7.56 (d, J 8.4 Hz,1H), 7.35 (d, J 1.6 Hz, 1H), 7.24 (s, 1H), 7.09 (d, J 8.4 Hz, 1H), 4.36(q4, J 6.8 Hz, 2H), 4.01 (s, 3H), 1.41 (t, J 6.8 Hz, 3H). 13C NMR(CDCl3) d 161.8 [C], 139.8 [C], 130.9 [C], 128.7 [C], 124.2 [C], 123.4[CH], 121.4 [CH], 110.1 [CH], 110.0 [CH], 60.6 [CH2], 31.7 [CH3], 14.3[CH3].

References:

Damont, Annelaure;Marguet, Frank;Puech, Frédéric;Dollé, Frédéric [European Journal of Medicinal Chemistry,2015,vol. 101,art. no. 8017,p. 736 - 745]

27034-51-1 Synthesis

27034-51-1
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616-38-6 Synthesis