Structure of 145349-76-4
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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. : | 145349-76-4 |
Formula : | C8H11BO2S |
M.W : | 182.05 |
SMILES Code : | OB(C1=CC=C(SCC)C=C1)O |
MDL No. : | MFCD01318146 |
InChI Key : | LMUASBOUSAMURX-UHFFFAOYSA-N |
Pubchem ID : | 2734353 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With cesium fluoride;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; for 3.0h;Heating / reflux; | A mixture of the product from step (i) (2G), 4- (ETHYLTHIO) PHENYLBORONIC ACID (1. 5G), cesium fluoride (2g) and Pd (DPPF) CL2 (0.2g) in dioxane (40ml) was heated under reflux for 3h. After cooling the mixture was partitioned between diethylether and water. The organics were separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica ELUTING WITH 5% ETOAC/ISO-HEXANE. YIELD 0.92g MS: APCI (+ve): 379/381 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.4% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 2.0h;Inert atmosphere; | The compound of example 203 (0.200 g, 0.537 mmol) was treated with 4- (ethylthio)phenylboronic acid (0.117 g, 0.645 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.027 mmol) and sodium carbonate (0.111 g, 0.806 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.100 g (42.4 %);1H NMR (DMSO-de, 300 MHz): δ 1.30 (t, 3H, J =6.0 Hz, CH3), 3.06 (q, 2H, J =6.0 Hz, CH2), 3.91 (s, 3H, OCHs), 6.94 (d, 1H, J =6.0 Hz, Ar), 7.49 (d, 2H, J =3.0 Hz, Ar), 7.73 (d, 2H, J =3.0 Hz, Ar), 7.91 (s, 1H, Ar), 8.03 (s, 1H, Ar), 8.15 (dd, 1H, J =1.2 Hz, J =5.1 Hz, Ar), 8.59 (d, 1H, J =3.0 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 430.6 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux; | General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux; | General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With dmap; 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); potassium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; at 70℃; for 24.0h; | To a 25 mL reaction tube, 164 mg (0.9 mmol) of 4-ethylthiophenylboronic acid, 6.6 mg (5 mol%, mol%Refers to the percentage of molar ratio of NiCl2DME to compound B) NiCl2DME (dimethylethyl ether ether chloride), 5.4Mg (5 mol%, mol% refers to the percentage of phen and the molar ratio of compound B) phen (1,10'-phenanthroline), 7.4 mg (5Mol%, mol% refers to the percentage of DMAP and compound B molar) DMAP (4-dimethylaminopyridine), 166 mg(1.2 mmol) of K2CO3, 2 mL of ethylene glycol dimethyl ether, 1.7 mL of 1,4-dioxane, injection of 300 uL of CH2FBr in 1,4-Dioxane solution (concentration: 2M, 0.6 mmol) was added, and the mixture was stirred at 70 C for 24 hours.The spectral yield was 68%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
150 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 110℃; for 0.166667h;Inert atmosphere; | Under argon, 24 mg (0.029 mmol) [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium(II) was added to a mixture of 150 mg (0.29 mmol) 2-(morpholin-4-yl)-8-[1-(tetrahydro-2H-pyran-2- yl)-1H-pyrazol-5-yl]-1,7-naphthyridin-4-yl trifluoromethanesulfonate and 106 mg (0.58 mmol) [4- (ethylsulfanyl)phenyl]boronic acid in 2.1 ml dioxane and 381 mg (1.17 mmol) caesium carbonate. The mixture was stirred at 110 C for 10 minutes. After cooling, the reaction mixture was dilutedwith ethyl acetate and an aqueous solution of sodium chloride. The mixture was extracted with ethyl acetate (2x) and the combined organic phases were filtered using a Whatman filter. The organic phase was concentrated and residue was purified by column chromatography (DCM / ethanol 0% - 30%) to give 150 mg (0.03 mmol) of the desired product, containing slight impurities, that was used without further purifications. |
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