| Identification | Back Directory | [Name]
4-Bromo-2-fluoro-N-methylbenzamide | [CAS]
749927-69-3 | [Synonyms]
SKL778
Enzalutamide Impurity 14
N-METHYL 4-BROMO-2-FLUORO
Enzalutamide EP Impurity B
N-Methyl 4-bromo-2-fluorobenzamide
4-Bromo-2-fluoro-N-methylbenzamide
BenzaMide, 4-broMo-2-fluoro-N-Methyl-
4-Bromo-2-fluoro-N-methylbenzamide
4-Bromo-2-fluoro-N-methylbenzamide(For export only) | [EINECS(EC#)]
808-257-8 | [Molecular Formula]
C8H7BrFNO | [MDL Number]
MFCD09878362 | [MOL File]
749927-69-3.mol | [Molecular Weight]
232.06 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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