Ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate Chemical Properties

Melting point:

>192°C (dec.)

Boiling point:

570.6±50.0 °C(Predicted)

Density 

1.44±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Sparingly, Heated)

pka

7.60±0.40(Predicted)

form 

Solid

color 

White to Light Brown

InChI

InChI=1S/C19H18BrNO3S/c1-3-24-19(23)18-13-9-17(22)14(20)10-15(13)21(2)16(18)11-25-12-7-5-4-6-8-12/h4-10,22H,3,11H2,1-2H3

InChIKey

DAFNNZWQTJQQAP-UHFFFAOYSA-N

SMILES

N1(C)C2=C(C=C(O)C(Br)=C2)C(C(OCC)=O)=C1CSC1=CC=CC=C1

Safety Information

HazardClass 

IRRITANT

Ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate Usage And Synthesis

Uses

6-Bromo-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-1H-indole-3-carboxylic Acid Ethyl Ester is used to prepare anti-hepatitis B virus activities of Et bromohydroxyindolecarboxylates.

Synthesis

To 900 mL of methanol was added 30 g of sodium hydroxide (0.75 mol) and stirred until completely dissolved to form a clarified solution. Subsequently, 39.7 g of benzenethiol (0.36 mol) was added to this solution and the reaction was continued with stirring for 2 hours. Next, 130 g of ethyl 1-methyl-2-(bromomethyl)-5-acetoxy-6-bromoindole-3-carboxylate (0.30 mol) was added and the reaction was continued with stirring for 3 hours. Upon completion of the reaction, the reaction mixture was neutralized with acetic acid and a large amount of solid was observed to precipitate. The mixture was allowed to stand, the solid was collected by filtration and the filter cake was washed with cold water. Finally, the crude product was recrystallized from ethyl acetate and dried to give 114.5 g of ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylthiomethyl)indole-3-carboxylate in 90.8% yield.

References

[1] Pharmaceutical Chemistry Journal, 1993, vol. 27, # 1, p. 75 - 76
[2] Khimiko-Farmatsevticheskii Zhurnal, 1993, vol. 27, # 1, p. 70 - 71
[3] Patent: CN106083691, 2016, A. Location in patent: Paragraph 0025; 0059
[4] Patent: US5198552, 1993, A

Ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate(131707-24-9)Related Product Information

• Tribenuron methyl
• Urethane
• Ethyl benzoylformate
• Ethyl cyanoformate
• CHLOROPHOSPHONAZO III
• Methyl salicylate
• N-Ethylmethylamine
• Cyclohexanecarboxylic acid ethyl ester
• Ethyl formate
• Indole
• Thiophanate-methyl
• Methyl
• Methyl bromide
• Methyl indole-3-carboxylate
• 1-Methyl-1H-indole-3-carboxylic acid
• 2-METHYL-1H-INDOLE-3-CARBOXYLIC ACID
• 1,2-DIMETHYL-1H-INDOLE-3-CARBOXALDEHYDE
• 1-Methylindole-3-carboxaldehyde