Structure of 19240-91-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 19240-91-6 |
Formula : | C7H5BrCl2O |
M.W : | 255.92 |
SMILES Code : | COC1=C(Cl)C=C(Br)C=C1Cl |
MDL No. : | MFCD10699182 |
Boiling Point : | No data available |
InChI Key : | OAYSFAKCFYRCRU-UHFFFAOYSA-N |
Pubchem ID : | 12963416 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.9% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; | Step 2: Preparation of 5-bromo-1,3-dichloro-2-methoxybenzene A mixture of 4-bromo-2,6-dichlorophenol (10 g, 41.67 mmol), K2CO3 (11.5 g, 83.3 mmol) and CH3I (8.88 g, 62.5 mmol) in DMF (100 mL) was stirred at rt for 16 h. TLC (EtOAc/petroleum ether=1:2) indicated complete consumption of 4-bromo-2,6-dichlorophenol. The reaction mixture was poured into water (300 mL). The aqueous phase was extracted with EtOAc (2*100 mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated in vacuo to give crude 5-bromo-1,3-dichloro-2-methoxybenzene, which was purified by column chromatography (silica gel, EtOAc/petroleum ether=1:5) to yield the ether product (9 g, yield 84.9%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.45 (s, H), 3.91 (s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.4% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 70℃; for 16h;Inert atmosphere; | Step 3: Preparation of 2-(3,5-dichloro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane A mixture of 5-bromo-1,3-dichloro-2-methoxybenzene (1 g, 3.94 mmol), bis(pinacolato)diboron (1.46 g, 5.83 mmol), Pd(dppf)Cl2(0.135 g, 0.19 mmol), KOAc (1.13 g, 11.6 mmol) in 1,4-dioxane (20 mL) was degassed with N2 for 5 min. The reaction mixture was stirred at 70 C. for 16 h. TLC (EtOAc/Petroleum ether=1:5) indicated complete consumption of the bromo starting material. The reaction mixture was poured into water (40 mL) and extracted with EtOAc (3*70 mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated in vacuo to give crude product, which was purified by column chromatography (silica gel, EtOAc/petroleum ether=1:10) to get the pure boron compound (0.5 g, yield 42.4%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.71 (s, 2H), 3.91 (s, 3H), 1.33 (s, 12H) ppm. |
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