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CAS No. : | 63697-96-1 | MDL No. : | MFCD05664348 |
Formula : | C9H6O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BGMHQBQFJYJLBP-UHFFFAOYSA-N |
M.W : | 130.14 | Pubchem ID : | 2771645 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
99% | With hydrogen; triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In acetonitrile; at 20 - 75℃;Inert atmosphere;Product distribution / selectivity; | Method 4; 4-(4-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzyl) morpholine; A. 4-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzaldehyde; 4-((4-(5,5-Dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)benzaldehyde was prepared following the method described in Method 3 steps A-C to yield 50.O g (99% yield) of the title compound as a yellow solid. LC-MS: [M+H]+ 319.0 1H NMR (400 MHz, CDCl3) δ: ppm 10.02 (s, IH), 7.95 (d, 2H), 7.79 (m, 4H), 7.66 (d, 2H), 3.78 (s, 4H), 1.00 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 0.5h; | General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7. | |
In ethanol; at 60℃; for 0.5h; | General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | General procedure: General synthetic procedure for 3a/3b/3c: 6-Bromocoumarin(0.5 g, 2.23 mmol), (4-ethynyl)benzaldehyde (0.29 g, 2.23 mmol)were dissolved in THF-triethylamine (1:1, v/v, 120 mL) and themixture was deaerated for 10 min with nitrogen bubbling and thenPd(PPh3)2Cl2 (31 mg, 2mol%), PPh3 (23 mg, 4 mol%)and CuI (8 mg,2mol%) were added. The solution was deaerated for an additional5 min; after that, reaction was left under nitrogen at 60C for 12 h.After completion of the reaction, the reaction mixture was cooledat room temperature and the solvent was evaporated. The crudeproduct was dissolved in CH2Cl2 and purified by a columnchromatography on a silica gel using (chloroform) as an eluent.Synthesis of 3a. Yield, 61% (0.37 g), 1H NMR (600 MHz, CDCl3) d10.04 (s, 1H,CHO), 7.89 (d, J = 8.25, 2H, aromatic), 7.70-7.68 (m,5H, aromatic), 7.35 (d, J = 9.17, 1H, aromatic), 6.48 (d, J = 9.55, 1H,aromatic).13C (150 MHz, CDCl3) d 192.67, 159.58, 153.76, 143.58,135.70, 134.89, 132.15, 131.81, 129.82, 127.88, 119.28, 117.80, 117.35,117.30, 91.58, 88.79. MS (m/z) 275 (M + H). | |
58% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; for 8h;Reflux; Inert atmosphere; | General procedure: The resulting bromocoumarin was reacted with 4-ethynylbenzaldehyde in the presence of Pd (PPh3) 2Cl2 and CuI in THF / triethylamine (1: 1 v / v)Was refluxed in N2 atmosphere (atm) for 8 hours,Ethynyl) benzaldehyde [4 - ((2-oxo-2H-chromen-6-yl) ethynyl) benzaldehyde] Ethynyl) benzaldehyde, 4 - ((2-oxo-2H-chromen-7-yl) ethynyl) benzaldehyde,(3a, 3b, 3c) was reacted with 4 - ((2-oxo-2H-chromen-8- yl) ethynyl) benzaldehyde Respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | General procedure: General synthetic procedure for 3a/3b/3c: 6-Bromocoumarin(0.5 g, 2.23 mmol), (4-ethynyl)benzaldehyde (0.29 g, 2.23 mmol)were dissolved in THF-triethylamine (1:1, v/v, 120 mL) and themixture was deaerated for 10 min with nitrogen bubbling and thenPd(PPh3)2Cl2 (31 mg, 2mol%), PPh3 (23 mg, 4 mol%)and CuI (8 mg,2mol%) were added. The solution was deaerated for an additional5 min; after that, reaction was left under nitrogen at 60C for 12 h.After completion of the reaction, the reaction mixture was cooledat room temperature and the solvent was evaporated. The crudeproduct was dissolved in CH2Cl2 and purified by a columnchromatography on a silica gel using (chloroform) as an eluent. |
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