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[ CAS No. 273731-82-1 ]

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Chemical Structure| 273731-82-1
Chemical Structure| 273731-82-1
Structure of 273731-82-1 * Storage: {[proInfo.prStorage]}

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Product Details of [ 273731-82-1 ]

CAS No. :273731-82-1 MDL No. :MFCD16295105
Formula : C11H15BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :222.05 g/mol Pubchem ID :-
Synonyms :

Safety of [ 273731-82-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 273731-82-1 ]

  • Downstream synthetic route of [ 273731-82-1 ]

[ 273731-82-1 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 273731-82-1 ]
  • [ 104-94-9 ]
  • C18H22BNO4 [ No CAS ]
  • 2
  • [ 273731-82-1 ]
  • [ 1393677-08-1 ]
  • (S)-2-(tert-butyloxycarbonylamino)-5-(fur-2-yl)pent-4-enoic acid [ No CAS ]
  • (S)-2-(tert-butyloxycarbonylamino)-5-(fur-2-yl)pent-4-enoic acid [ No CAS ]
  • 3
  • [ 273731-82-1 ]
  • [ 231278-20-9 ]
  • [ 231278-84-5 ]
YieldReaction ConditionsOperation in experiment
87% With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine; In methanol; for 8h;Reflux; Example 65-(4-(3-Chloro-4-(3-fluorobenzyloxy)phenylam ino)ch inazolin-6-yl)furan-2-carbaldehyde IIII (3.3 g, 6.42 mmol), 10 % Pd/C (78 mg, 0.07 mmol, 1.2 mol. %), methanol (45 ml), N,N-diisopropylethylamine (2.2 ml, 12.85 mmol, 2 equiv.) were added to the ester Vila (1.8 g, 8.35 mmol, 1.3 equiv.) and the resulting suspension was refluxed for 8 hours.After cooling to the room temperature the yellow suspension was filtered and washed with methanol (3 X 20 ml). The product was subsequently dissolved in THF (45 ml) and filtered through a kieselguhr layer, which, after evaporation of the solvent, WO 2014/059956 PCT/CZ2013/000132provided 2.6 g (87 %) of the title compound (I) as a yellow powdery substance. HPLCpurity: 95%1H NMR (500 MHz, DMSOd6): 5.27 (s, 2 H), 7.16-7.20 (m, I H), 7.28-7.35 (m, 3H)7.43 (d, J = 3.7 Hz, 1 H), 7.45-7.48 (m, I H), 7.71-7.74 (m, 2 H), 7.46 (d, J = 3.56 Hz,H), 7.85 (J = 8.7 Hz, 1H), 8.00 (J = 2.4 Hz, 1H), 8.29 (dd, J = 1.8 Hz, J = 8.7 Hz),8.59 (s, 1H), 8.99 (d, J= 1.5 Hz, IH), 9.67 (s, 1H), 10.14 (s, IH).
  • 4
  • [ 13529-27-6 ]
  • [ 61676-62-8 ]
  • [ 273731-82-1 ]
YieldReaction ConditionsOperation in experiment
Example I5-(4,4, 5, 5-Tetramethyl- 1, 3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (VIla)A 2.5M solution of butyllithium in hexanes (50 ml, 0.125 mol) was added to a solution of <strong>[13529-27-6]diethylacetal furan-2-carbaldehyde</strong> (17.0 g, 0.1 mol) in dimethoxyethane (100 mL) with a linear dispenser at the temperature of -50C during 1 hour and the mixture wasstirred under nitrogen at this temperature for 4 hours. Then, 2-isopropoxy-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (24.0 g, 0.129 mol) was added with a linear dispenser during 30 minutes and the mixture was stirred at -40C for 2 hours and then stirred without cooling under nitrogen for 4 hours (the internal temperature rose to 20C). 2.5M HCI (100 ml) was added dropwise to the dark reaction mixture and themixture was stirred at the room temperature for 30 minutes. After addition of ethyl acetate (200 ml), the organic layer was separated and the aqueous layer was shaken with ethyl acetate (2 x 25 ml). The combined organic fractions were washed with water (4 x 25 ml) and dried with MgSO4. 18.3 g of the crude product was obtained containing, according to HPLC, 96.8% of the desired compound in the form of ayellowish liquid. The product contained 2-3% of the corresponding boronic acid. If it is undesired, it can be easily removed by addition of a small amount of pinacol to a solution of the crude compound VIla in a suitable solvent.1H NMR (250 MHz, DMSOd6): 1.30(s, 12 H), 7.23(d, J= 3.6 Hz, IH), 7.51 (d, J3.6 Hz, I H), 9.71 ppm (s, 1 H).
  • 5
  • [ 273731-82-1 ]
  • [ 231277-92-2 ]
  • 6
  • [ 76-09-5 ]
  • [ 27329-70-0 ]
  • [ 273731-82-1 ]
YieldReaction ConditionsOperation in experiment
70% In tetrahydrofuran; at 20℃; for 2h; Example 25-(4,4, 5, 5-Tetramethyl- 1, 3,2-d ioxaborolan-2-yl)furan-2-carbaldehyde Vila5-Formylfuran-2-yl boronic acid (139 mg, 1.47 mmol) was suspended in dry THF (4.4 ml), subsequently anhydrous pinacol (174 mg, 1.47 mmol, I equiv.) was added and the reaction mixture was stirred at the room temperature for 2 hours. The resulting solution was filtered and evaporated at a reduced pressure, which provided 228 mg (70%) of the title compound VIla in the form of yellowish oil.1H NMR (250 MHz, DMSO-d6): 1.30 (s, 12 H), 7.23 (d, J = 3.60 Hz, IH), 7.51 (d, J =3.60 Hz, I H), 9.71 ppm (s, 1 H).
  • 7
  • [ 273731-82-1 ]
  • [ 171082-32-9 ]
  • C22H22BN3O4 [ No CAS ]
  • 8
  • [ 273731-82-1 ]
  • tert-butyl ((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl)methyl)carbamate [ No CAS ]
  • 9
  • [ 273731-82-1 ]
  • C11H16BNO4 [ No CAS ]
  • 10
  • [ 273731-82-1 ]
  • C11H18BNO3*C2HF3O2 [ No CAS ]
  • 11
  • [ 1899-24-7 ]
  • [ 73183-34-3 ]
  • [ 273731-82-1 ]
  • 12
  • [ 611-32-5 ]
  • [ 273731-82-1 ]
  • 4-(quinolin-8-ylmethyl)furan-2-carbaldehyde [ No CAS ]
  • 13
  • [ 273731-82-1 ]
  • [ 2927-71-1 ]
  • 5-(2-chloro-5-fluoropyrimidin-4-yl)furan-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate; In 1,4-dioxane; ethanol; water; at 80℃; for 2h;Inert atmosphere; General procedure: Corresponding intermediates (21a-21f) (1.3 equiv), 2-chloro-5-R8pyrimidine, PdCl2(dppf) (0.05 equiv) and potassium carbonate (2.5equiv) were dissolved in dioxane/EtOH/water (V/V/V, 7/3/4). The reaction liquid was stirred under nitrogen atmosphere at 80 C for 2 h.After the reaction was complete, the reaction liquid was concentrated under reduced pressure and purified by silica gel column with the mobile phase system (petroleum ether: ethyl acetate = 60:40). Finally, intermediates 22a-22i were obtained. 4.1.22.1. 6-(2-chloro-5-fluoropyrimidin-4-yl)-1-methyl-1H-pyrazolo[4,3-b]pyridine (22a). Yellow solid, yield 72%. 1H NMR (400 MHz, CDCl3) δ:8.91 (d, J = 2.1 Hz, 1H), 8.55 - 8.49 (m, 1H), 8.39 (s, 1H), 8.02 (d, J =0.6 Hz, 1H), 3.91 (s, 3H).
  • 14
  • [ 273731-82-1 ]
  • 2-chloro-5-fluoro-4-(5-(pyrrolidin-1-ylmethyl)furan-2-yl)pyrimidine [ No CAS ]
  • 15
  • [ 273731-82-1 ]
  • 1-((5-(2-chloro-5-fluoropyrimidin-4-yl)furan-2-yl)methyl)indoline [ No CAS ]
Historical Records

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[ 273731-82-1 ]

Organoboron

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Aldehydes

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Esters

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Related Parent Nucleus of
[ 273731-82-1 ]

Furans

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