METHYL4-BROMOFURAN-2-CARBOXYLATE Chemical Properties

Melting point:

42-44 °C

Boiling point:

228℃

Density 

1.623

Flash point:

92℃

storage temp. 

2-8°C

Appearance

White to yellow Solid

InChI

InChI=1S/C6H5BrO3/c1-9-6(8)5-2-4(7)3-10-5/h2-3H,1H3

InChIKey

RKEXKLRKXLRNMV-UHFFFAOYSA-N

SMILES

O1C=C(Br)C=C1C(OC)=O

METHYL4-BROMOFURAN-2-CARBOXYLATE Usage And Synthesis

Uses

Methyl 4-Bromofuran-2-carboxylate is used to prepare pyrimidinamines and pyridinamines as adenosine receptor modulators for treatment of CNS disorders.

Synthesis

General procedure for the synthesis of methyl 4-bromofuran-2-carboxylate from methyl 4,5-dibromofuran-2-carboxylate: isopropylmagnesium chloride (2M solution of THF, 38 mL) was added slowly and dropwise to a solution of methyl 4,5-dibromofuran-2-carboxylate (14.2 g, 50 mmol) in anhydrous THF (100 mL) at -40 °C and under nitrogen protection. The reaction mixture was stirred continuously at the same temperature for 1 h. The reaction was subsequently quenched by the addition of water (50 mL). The precipitate was collected by filtration and the filtrate was extracted by partitioning with ethyl acetate and water. The organic phase was washed twice with saturated saline, dried over anhydrous sodium sulfate and purified by silica gel column chromatography to afford the target product, methyl 4-bromofuran-2-carboxylate (11a), as a yellow solid (9 g, 89% yield).1H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.51 (s, 1H), 3.82 (s, 3H).

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 47 - 58
[2] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 26, p. 5397 - 5403
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2019 - 2024
[4] Patent: CN105503832, 2016, A. Location in patent: Paragraph 0065; 0066; 0069; 0070
[5] Patent: WO2008/98104, 2008, A1. Location in patent: Page/Page column 217

METHYL4-BROMOFURAN-2-CARBOXYLATE(58235-80-6)Related Product Information

• METHYL 4-(1H-IMIDAZOL-1-YL)BENZENECARBOXYLATE
• 4-BROMOFURAN-2-CARBOXYLICACID
• 4-Bromogramine
• 2-(4-bromo-1H-indol-3-yl)ethanamine
• 4-bromoquinoline-6-carboxylic acid
• ethyl 4-broMoquinoline-6-carboxylate
• Methyl 4-bromoquinoline-6-carboxylate
• 4-bromoisoindolin-1-one
• Carbamic acid, N-(4-bromo-2-thiazolyl)-, 1,1-dimethylethyl ester
• methyl 4-bromoquinoline-8-carboxylate