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CAS No. : | 1150561-61-7 | MDL No. : | MFCD12026094 |
Formula : | C13H17BF3NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GNJXUHQYHOJYMP-UHFFFAOYSA-N |
M.W : | 303.09 | Pubchem ID : | 46739459 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In water; acetonitrile at 125℃; for 0.25h; Microwave irradiation; | (S)-3-[4-(5-Chloro-6-methoxy-pyridin-3-yl)-quinolin-6-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester General procedure: 3-chloro-2-methoxypyridine-5-boronic acid (CAS registry 942438-89-3) (57 mg, 0.30 mmol) followed by K3P04 (CAS registry 7778-53-2) (97.0 mg, 0.46 mmol), PdCI2(PPh3)2 (CAS registry 13965-03-2) (10.7 mg, 0.01 mmol) and finally water (0.2 ml) were added to a mixture of ((S)-3-(4-bromo-quinolin-6-yloxy)-pyrrolidine-1 -carboxylic acid tert-butyl ester (120 mg, 0.30 mmol) in acetonitrile (2 ml) in a microwave tube. The tube was capped and the reaction mixture was heated in a microwave reactor at 125°C for 15 min. The mixture was diluted with DCM and washed with sat. aq. NaHC03 soln. and the organic solution was separated through a phase separating cartridge affording a yellow solution. The crude product was purified by flash chromatography on silica gel (cyclohexane / EtOAc 100:0 to 0:100) to provide the title compound (1 14 mg, 82% yield). HPLC RtMO1=1.27 min; ESIMS: 456, 458 [(M+H)+].1H NMR (400 MHz, CDCI3): δ 8.80 (d, 1 H), 8.33 (d, 1 H), 8.16 (d, 1 H), 8.04 (d, 1 H), 7.49 (dd, 1 H), 7.46 (d, 1 H), 7.10 (br. s., 1 H) , 5.06 (m, 1 H), 4.03 (s, 3H), 3.57-3.36 (m, 4H), 2.10 (br. s., 2H ), 1.37 (d, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 120℃; for 3h;Inert atmosphere; | <strong>[1214377-42-0]3-trifluoromethyl-2-methoxy-5-bromopyridine</strong> (0.50 g, 1.95 mmol)0.12 g (2.34 mmol) of diphenylolate borate,0.57 g (5.85 mmol) of potassium acetate and 0.10 g (0.14 mmol) of Pd (dppf) Cl2 in 100 mL eggplant vials, Adding dioxane 12mL, nitrogen protection, heating at 120 reflux 3h,To give the product containing 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5-methanesulfonamido-6-methoxypyridine Of the reaction system, cooled to room temperature,To this system was added 0.37 g (1.63 mmol) of 2-amino-6-bromobenzothiazole,Potassium carbonate 0.67 g (4.88 mmol)Pd (dppf) Cl2 0.15 g (0.20 mmol) and water 3 mL,Nitrogen protection,120 heating reflux 6h,Cooled to room temperature, steamed to remove the solvent, silica gel column chromatography separation and purification,Eluent (V / V): chloroform / methanol = 50/1, gave 0.40 g of a white solid, yield: 75.43% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.43% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water at 120℃; for 6h; Inert atmosphere; | 18.1 (S) -N1- [6- (5-Trifluoromethyl-6-methoxy-3-pyridyl) -2-benzothiazolyl] -1,2-tetrahydropyrrole dicarboxamide (T18) synthesis 3-trifluoromethyl-2-methoxy-5-bromopyridine (0.50 g, 1.95 mmol)0.12 g (2.34 mmol) of diphenylolate borate,0.57 g (5.85 mmol) of potassium acetate and 0.10 g (0.14 mmol) of Pd (dppf) Cl2 in 100 mL eggplant vials, Adding dioxane 12mL, nitrogen protection, heating at 120 reflux 3h,To give the product containing 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5-methanesulfonamido-6-methoxypyridine Of the reaction system, cooled to room temperature,To this system was added 0.37 g (1.63 mmol) of 2-amino-6-bromobenzothiazole,Potassium carbonate 0.67 g (4.88 mmol)Pd (dppf) Cl2 0.15 g (0.20 mmol) and water 3 mL,Nitrogen protection,120 heating reflux 6h,Cooled to room temperature, steamed to remove the solvent, silica gel column chromatography separation and purification,Eluent (V / V): chloroform / methanol = 50/1, gave 0.40 g of a white solid, yield: 75.43% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 6 h / 120 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 24 h / 20 °C 2.2: 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium phosphate / water; acetonitrile / 0.25 h / 125 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium phosphate / water; acetonitrile / 0.25 h / 125 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 3: N-[([(1E)-1-cyano-2-ethoxy-2-oxoethylidene]amino}oxy)(morpholin-4-yl)methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water Reflux; Inert atmosphere; | 4.1.4 (S)-tert-Butyl 3-((6-(6-methoxy-5-(trifluoromethyl)pyridin-3-yl)quinazolin-4-yl)amino)piperidine-1-carboxylate (12c) To a solution mixture of 11 (350mg, 0.86mmol) in DME/H2O (8mL/2mL), were added the 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl) pyridine (561mg, 1.85mmol), PdCl2(dppf) (73.2mg, 0.1mmol) and Na2CO3 (182mg, 1.72mmol). The mixture was refluxed under N2 atmosphere for 4h and then the mixture was concentrated and purified by silica gel chromatography (CH2Cl2/CH3OH, 20:1) to give compound 12c (510mg, 81%) as a brown solid. MS (ESI) m/z: [M+H]+=504.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water / Reflux; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water / Reflux; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.7% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,2-dimethoxyethane; lithium hydroxide monohydrate for 2.5h; Reflux; Inert atmosphere; | 14 (S)-N-butyl-2-((6-(6-methoxypyridin-3-yl)quinazolin-4-yl)amino)propanamide (Compound 1) General procedure: Take the intermediate (S)-2-((6-bromo-4-quinazolinyl)amino)-N-butylpropionamide (280 mL, 0.80 mmol), 2-methoxy-5-pyridineboronic acid (184 mg , 1.20 mmol), Na2CO3 (170 mg, 1.60 mmol), PdCl2(dppf) (71 mg, 0.097 mmol), ethylene glycol dimethyl ether (8 mL) and H2O (2 mL) N2 protection, heated to reflux for about 2.5 h, TLC showed The reaction is complete. After cooling, evaporation to dryness under reduced pressure was performed by column chromatography to obtain 65 mg of a white solid with a yield of 63.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33.4% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,2-dimethoxyethane; lithium hydroxide monohydrate for 2.5h; Reflux; | 24 (S)-N-butyl-2-((6-(6-methoxypyridin-3-yl)quinazolin-4-yl)amino)propanamide (Compound 1) General procedure: Take the intermediate (S)-2-((6-bromo-4-quinazolinyl)amino)-N-butylpropionamide (280 mL, 0.80 mmol), 2-methoxy-5-pyridineboronic acid (184 mg , 1.20 mmol), Na2CO3 (170 mg, 1.60 mmol), PdCl2(dppf) (71 mg, 0.097 mmol), ethylene glycol dimethyl ether (8 mL) and H2O (2 mL) N2 protection, heated to reflux for about 2.5 h, TLC showed The reaction is complete. After cooling, evaporation to dryness under reduced pressure was performed by column chromatography to obtain 65 mg of a white solid with a yield of 63.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.5% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,2-dimethoxyethane; lithium hydroxide monohydrate for 2.5h; Reflux; Inert atmosphere; | 22 (S)-N-butyl-2-((6-(6-methoxypyridin-3-yl)quinazolin-4-yl)amino)propanamide (Compound 1) General procedure: Take the intermediate (S)-2-((6-bromo-4-quinazolinyl)amino)-N-butylpropionamide (280 mL, 0.80 mmol), 2-methoxy-5-pyridineboronic acid (184 mg , 1.20 mmol), Na2CO3 (170 mg, 1.60 mmol), PdCl2(dppf) (71 mg, 0.097 mmol), ethylene glycol dimethyl ether (8 mL) and H2O (2 mL) N2 protection, heated to reflux for about 2.5 h, TLC showed The reaction is complete. After cooling, evaporation to dryness under reduced pressure was performed by column chromatography to obtain 65 mg of a white solid with a yield of 63.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 5h; Inert atmosphere; |
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