4-Bromo-2-fluoro-N-methylbenzamide Chemical Properties

Melting point:

125.0 to 129.0 °C

Boiling point:

284.8±30.0 °C(Predicted)

Density 

1.545±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

13.76±0.46(Predicted)

color 

White to Off-White

InChIKey

BAJCFNRLEJHPTQ-UHFFFAOYSA-N

CAS DataBase Reference

749927-69-3

Safety Information

HS Code 

2924297099

4-Bromo-2-fluoro-N-methylbenzamide Usage And Synthesis

Uses

4-Bromo-2-fluoro-N-methylbenzamide is an intermediate in the synthesis of MDV 3100 (M199800), is an androgen-receptor antagonist that blocks androgens from binding to the androgen receptor and prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex.

Synthesis

Step 1: Synthesis of 4-bromo-2-fluoro-N-methylbenzamide To a 100 mL round-bottomed flask were added 4-bromo-2-fluorobenzoic acid (3.0 g, 13.7 mmol), 2 M aqueous methylamine (34.3 mL, 68.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI, 6.6 g, 34.25 mmol), 1-hydroxybenzotriazole (HOBt, 2.8 g 20.6 mmol), N,N-diisopropylethylamine (DIPEA, appropriate amount) and N,N-dimethylformamide (DMF, 50 mL). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL). The aqueous phase was separated and the organic phase was extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent ethyl acetate/petroleum ether (1:3, v/v) to afford the title compound 4-bromo-2-fluoro-N-methylbenzamide as a white solid (2.34 g, 74% yield). Mass spectrum (MS): [M+H]+ 232.

References

[1] Patent: CN108329236, 2018, A. Location in patent: Paragraph 0026; 0035; 0036; 0038
[2] Patent: WO2014/32498, 2014, A1. Location in patent: Page/Page column 9
[3] Patent: WO2004/74270, 2004, A2. Location in patent: Page 44
[4] Patent: US2005/176701, 2005, A1. Location in patent: Page/Page column 21
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6486 - 6489

4-Bromo-2-fluoro-N-methylbenzamide(749927-69-3)Related Product Information

• 4-amino-2-fluoro-N-methylbenzamide
• 4-[1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-1-methyl-ethylamino]-2-fluoro-N-
• Enzalutamide Impurity 7
• 4-isothiocyanato-2-(trifluoroMethyl)benzonitrile
• Enzalutamide Impurity 7
• [2H6]-Enzalutamide
• N-desMethyl EnzalutaMide
• Enzalutamide carboxylic acid
• 4-(2-CYANOPROPAN-2-YLAMINO)-2-FLUORO-N-METHYLBENZAMIDE
• Methyl 4-bromo-2-fluorobenzoate
• Enzalutamide
• 4-[3-[4-Cyano-3-(trifluoroMethyl)phenyl]-5,5-diMethyl-4-oxo-2-thioxo-1-iMidazolidinyl]-2-fluoro-N-(Methyl-d3)benzaMide
• 4-[3-(4-Cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-N-methylbenzamide
• 4-Bromo-2-fluorobenzoic acid
• methyl 2-fluoro-4-((1-methoxy-2-methyl-1-oxopropan-2-yl)amino)benzoate
• EnzalutaMide IMpurity
• Enzalutamide
• 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluorobenzoic acid methyl ester