537013-51-7 Usage
Description
4-BROMO-2,6-DIFLUOROBENZYLALDEHYDE is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals and organic compounds. It is characterized by its unique molecular structure, which features a benzene ring with a bromine atom at the 4th position, and two fluorine atoms at the 2nd and 6th positions. This structure endows the compound with specific chemical properties that make it valuable in a range of applications.
Uses
Used in Organic Synthesis:
4-BROMO-2,6-DIFLUOROBENZYLALDEHYDE is used as a key intermediate in the organic synthesis of various compounds. Its unique structure allows for a wide range of chemical reactions, making it a versatile building block for the creation of new molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
4-BROMO-2,6-DIFLUOROBENZYLALDEHYDE is used as a pharmaceutical intermediate for the development of new drugs. Its specific chemical properties enable the creation of novel drug candidates with potential therapeutic benefits. 4-BROMO-2,6-DIFLUOROBENZYLALDEHYDE plays a crucial role in the research and development of pharmaceuticals, contributing to the advancement of medical treatments.
Used in Laboratory Research and Development:
4-BROMO-2,6-DIFLUOROBENZYLALDEHYDE is employed in laboratory research and development as a valuable tool for exploring new chemical reactions and synthesizing novel compounds. Its unique structure and reactivity make it an essential component in the quest for new discoveries and innovations in the fields of chemistry and pharmaceuticals.
Used in Chemical Production Processes:
4-BROMO-2,6-DIFLUOROBENZYLALDEHYDE is utilized in chemical production processes as a vital intermediate for the synthesis of various chemicals and materials. Its unique properties and reactivity contribute to the efficient and cost-effective production of a wide range of products, from pharmaceuticals to specialty chemicals.
Synthesis
n-Butyl lithium (0.64ml, 1.2 mmol) was added drop wise to a solution of diisopropyl amine (0.25 mL, 1.5 mmol) in dry THF at -78°C under nitrogen atmosphere over a period of 5 minutes. The reaction mixture was stirred at -20°C for 30 minutes. To this was added 5-bromo-benzo[b]thiophene (200 mg, 0.938 mmol) in dry THF at -78°C, continued stirring for a further 30 minutes at -78°C, followed by the addition of N-chlorosuccinamide (225 mg, 1.68 mmol) in dry THF at -78°C. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% hexane). The reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was dried over sodium sulfate and concentrated to afford the crude product. Purification by column chromatography on silica gel (100% hexane) afforded the product. Preparation of Intermediate 4-Bromo-2,6-difluoro-benzaldehyde (I-26a): Using analogous reaction condition and reagents as described in Example 20 for the preparation of 1-20a above, 1-bromo-3,5-difluoro-benzene (2 g, 2.10.36 mmol) in THF was reacted with DMF (1.43 g,19.68 mmol), n-butyl lithium (1.56 ml, 12.4 mmol) and diisopropyl amine (0.57 mL, 15.5 mmol) to afford crude product. Purification by column chromatography on silica gel (2% ethyl acetate in hexane) afforded 1.35 g of the product (61% yield). 1H NMR (CDCl3, 300 MHz): δ 11.5-11.0 (s, 1H), 7.4-7.2 (dd, 2H).
Check Digit Verification of cas no
The CAS Registry Mumber 537013-51-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 5,3,7,0,1 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 537013-51:
(8*5)+(7*3)+(6*7)+(5*0)+(4*1)+(3*3)+(2*5)+(1*1)=127
127 % 10 = 7
So 537013-51-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H3BrF2O/c8-4-1-6(9)5(3-11)7(10)2-4/h1-3H
537013-51-7Relevant articles and documents
Efficient Manufacturing Process for the Selective Estrogen Receptor Degrader GDC-9545 (Giredestrant) via a Crystallization-Driven Diastereoselective Pictet-Spengler Condensation
Angelaud, Rémy,Chung, Cheol K.,Clagg, Kyle,Dalziel, Michael E.,Fettes, Alec,Finet, Laure,Gosselin, Francis,Jenny, Christian,Kammerer, Michael,Lim, Ngiap-Kie,Mack, Kyle A.,McClory, Andrew,Wuitschik, Georg,Xu, Jie,Zhang, Haiming
, (2021/11/24)
GDC-9545 is a selective estrogen receptor degrader that is being developed as a treatment for ER+/HER2- breast cancer. A robust, convergent manufacturing process for GDC-9545 was developed. The process features a Wenker aziridine synthesis to produce the key starting material tryptamine 11, a highly efficient C-N coupling between aminoazetidine 9 and 2,6-difluoro-4-bromobenzaldehyde diethyl acetal (33) to construct key intermediate 10, and a crystallization-driven diastereoselective Pictet-Spengler reaction to furnish the active pharmaceutical ingredient GDC-9545·tartrate.
First-Generation Asymmetric Synthesis of the Selective Estrogen Receptor Degrader GDC-9545 (Giredestrant) Featuring a Highly Efficient Pictet-Spengler Reaction and a C-N Coupling Reaction
Chung, Cheol K.,Clagg, Kyle,Gosselin, Francis,Lim, Ngiap-Kie,Wuitschik, Georg,Xu, Jie,Zhang, Haiming
, (2021/11/18)
An asymmetric synthesis of the selective estrogen receptor degrader GDC-9545 (1) is described. The synthesis features a Friedel-Crafts indole functionalization and a strain-release aminoazetidine formation to construct the two key starting materials 2 and 4, respectively, a diastereoselective Pictet-Spengler reaction (98% yield, 95:5 dr) to assemble the tetrahydrocarboline core, and a highly efficient Pd-catalyzed C-N coupling (90% yield) using [t-BuBrettPhos Pd(allyl)]OTf as the catalyst and DBU as the base to furnish the final C-N bond. This expedient route produces GDC-9545·tartrate active pharmaceutical ingredient in a longest linear sequence of six steps in 37% overall yield with 99.0 area % HPLC purity without chromatographic purification.
Inhibiting effect of trisubstituted pyrimidine derivative on protein kinase
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Paragraph 0020-0023, (2019/09/14)
The invention discloses a trisubstituted pyrimidine derivative with a structure shown as general formula (I), and pharmaceutically acceptable salt, ester or solvent compound thereof. The derivative isa protein kinase inhibitor, can be used individually or in combination with other drugs for cancer treatment, and has tremendous clinical application value. General formula (I) is shown as the specification.
