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CAS No. : | 55934-00-4 | MDL No. : | MFCD01861989 |
Formula : | C5H3Cl2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZMPYQKNNUHPTLT-UHFFFAOYSA-N |
M.W : | 147.99 | Pubchem ID : | 2736081 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 34.26 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.7 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 2.11 |
Log Po/w (WLOGP) : | 2.39 |
Log Po/w (MLOGP) : | 1.68 |
Log Po/w (SILICOS-IT) : | 2.73 |
Consensus Log Po/w : | 2.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.64 |
Solubility : | 0.338 mg/ml ; 0.00228 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.01 |
Solubility : | 1.44 mg/ml ; 0.00974 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.24 |
Solubility : | 0.0859 mg/ml ; 0.000581 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.2 |
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 |
---|---|---|
29% | With potassium carbonate;copper; In N,N-dimethyl-formamide; at 110℃; | General Procedure: To a 50 mL round bottom flask equipped with a stir bar were added 3,4- dichloropyridine (0.70 g, 4.73 mmol), piperazine-1-carboxylic acid tert-butyl ester (0.86 g, 4.73 mmol), copper powder (36 mg, 0.57 mmol), potassium carbonate (0.65 g, 4.73 mmol) and N,N-dimethylfbrrnamide (10 mL). The reaction mixture was stirred at 110 C overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and sequentially washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vauo. The crude residue was purified on silica gel using hexanesrethyl acetate = 80:20 to 50:50 in a gradient fashion, to give the desired product as a yellow solid (404 mg, 29 %). 1H NMR (300 MHz, CDCl3): delta 8.30 (bd, 2H), 6.74 (d, IH), 3.52 (m, 4H), 3.07 (m, 4H), 1.4 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Example 40 3-Chloro-4-[2-(2,4-dimethylphenoxy)propylamino]-2-methylpyridine Analogously to Example 35 from <strong>[55934-00-4]3,4-dichloropyridine</strong> and 2-(2,4-dimethylphenoxy)propylamine. After 2 hours at 180 C. the mixture was worked up. Yield: 63% 1 H-NMR (100 MHz, CD2 OD)=7.9 (d, 1H), 6.9 to 7.0 (m, 3H), 6.7 (d, 1H), 4.6 (m, 1H), 3.5 (m, 2H), 2.5 (s, 3H), 2.2 (s, 3H), 2.1 (s, 3H), 1.3 (d, 3H) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In isopropyl alcohol; | EXAMPLE 34 N-(3-Chloro-4-pyridinyl)-3-methyl-1H-indol-1-amine hydrochloride The title compound was prepared from 3-methyl-1H-indol-1-amine and <strong>[55934-00-4]3,4-dichloropyridine</strong> in isopropanol at 80 C. for 5 hours in substantially the same manner as in Example 1. Recrystallized from ethanol, m.p. 278-280 C. (decomp.). ANALYSIS: Calculated for C14 H12 ClN3.HCl: 57.16% C 4.45% H 14.29% N. Found: 57.20% C 4.44% H 14.28% N. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.9% | To a solution of 2,2,6, 6-tetramethylpiperidine (12.4 mL, 74.4 mmol) in diethylether (100 mL) at 0 C was added n-BuLi in hexane (2.5 M, 46 mL, 115 mmol) via a syringe over 15 min. The resulting solution was stirred at 0 C for 0.5 h and at -78 C for 0.5 h. To this mixture was added a mixture of <strong>[55934-00-4]3,4-dichloropyridine</strong> (10.00 g, 67.6 mmol) in diethylether (40 mL) via a syringe over 15 min. The resulting mixture was stirred at -78 C for 2 h before the addition of isocyanatotrimethylsilane (94% pure, 13.4 mL, 101.4 mmol). After the addition, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature for 2 h. The reaction mixture was quenched with acetic acid (13.52 g, 225.2 mmol) and 70 mL of water. The mixture was allowed to stir overnight, and the white solid that formed was collected through filtration and washed with water. The filtrate was extracted with EtOAc (50 mL x 3). The combined organic phase was washed with brine and dried over anhydrous Na2S04, then concentrated in vacuo. The residue was beaten by PE/EtOAc = 2/1 (100 mL) to give a white solid. The two parts of solid was got together to give the title compound (6.95 g, 53.9%).LC-MS (ESI, pos, ion): 191 [M+H]+;^ NMR ^OO MHz, CDCb) delta (ppm): 8.38 (d, J= 5.0 Hz, 1H), 7.59 (d, J= 5.0 Hz, 1H). | |
53.9% | n-BuLi (2.5 M n-hexane solution, 46 mL, 115 mmol) with a syringe at 0 CSlowly dropwise added to a solution containing 2,2,6,6-tetramethylpiperidine (12.4 mL, 74.4 mmol) in diethyl ether (100 mL).It?s about 15 minutes,The reaction solution was stirred at 0 C for 0.5 hours.Reduce to -78 C and stir for another 0.5 hours.Then, a solution containing <strong>[55934-00-4]3,4-dichloropyridine</strong> (10.00 g, 67.6 mmol) in diethyl ether (40 mL) was slowly added dropwise (about 15 minutes) to the above reaction solution.Stirring was continued for 2 hours at -78 C.Finally, trimethylsilyl isocyanate (94% pure, 13.4 mL, 101.4 mmol) was added to the above reaction solution.Stir to room temperature and stir for 2 hours.The reaction was quenched with acetic acid (13.52 g, 225.2 mmol) and water (70 mL).Stir at room temperature overnight,filter,The resulting white solid was washed with water and collected.The filtrate was extracted with EtOAc (50 mL x 3) and the organic phase was separated.Combine the obtained organic phases,Wash with saturated brine,After drying with anhydrous sodium sulfate,Concentrated under reduced pressure,The resulting residue was slurried in a solution of PE/EtOAc = 2 / 1 (100 mL) to give a white solid.The title compound (6.95 g, 53.9%) | |
49% | At -78C, n-BuLi (2.4 M, 19.5 mL, 31 mol, 1.15 eq) was added slowly in a dropwise manner into a solution of 2,2,6,6-tetramethylpiperidine (4.4 g, 31 mmol, 1.15 eq) in ether (50 mL), reacted for 2 h, a solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (4 g, 27 mol, 1.0 eq) in ether (5 mL) was then added into the reaction solution, reacted at - 78C for another 2 h, and trimethylsilyl isocyanate (95% pure, 5.6 mL, 40 mol, 1.5 eq) was added dropwise to the reaction system, warmed slowly to room temperature, and reacted for 2 h. The reaction was quenched by addition of acetic acid (5.4 g, 90 mmol) and water (27 mL), the mixture was stirred overnight, filtered and washed with a little ether to obtain 2.51 g (49%) of products. 1H NMR (400 MHz, d6-DMSO) delta 8.48 (d, J=5.2Hz, 1H), 8.07 (s, 1H), 7.82 (m, 2H). |
40% | To a solution of 2,2,6,6-tetramethylpiperidine (1.56 g, 11 mmol) in dry ether (20 mL) at 0 C was added n-BuLi (4.4 mL, 2.5 M in THF, 11 mmol) slowly. The reaction mixture was stirred at this temperature for 30 min before cooled to -78 C. A solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (1.48 g, 10 mmol) in dry ether (5 mL) was injected via syringe to the above reaction mixture and stirred for 2 h before trimethylsilyl isothiocyanate (15 mmol) was added. After warmed to room temperature, the reaction was quenched by the addition of HOAc (2 mL) and water (10 mL), and then let to stir overnight. The suspension was filtered and washed with cold water, giving the title compound as a gray solid (686 mg, 40%). 1H-NMR (DMSO-d6, 600 MHz) delta 8.50 (d, 1H,J = 5.2 Hz, ArH), 8.12 (br s, 1H, CONH2), 7.83 (d, 1H, J = 5.2 Hz, ArH), 7.82 (br s, 1H, CONH2). | |
39% | Alternatively, 3,4-dichloropicolinamide can be prepared directly from <strong>[55934-00-4]3,4-dichloropyridine</strong> according to the procedure described below.To a solution of 2,2,6,6-tetramethylpiperidine (31.1 g, 0.22 mol) in diethyl ether (400 mL) at 0 C. was added n-BuLi in hexane (1.6 M, 138.0 mL, 0.22 mol) via syringe over 15 min. The resulting solution was stirred at 0 C. for 0.5 h and at -78 C. for 0.5 h. To this mixture was then slowly added a solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (29.6 g, 0.20 mol) in diethyl ether (20 mL) via syringe over 15 min. The resulting mixture was stirred at -78 C. for 2 h before the addition of isocyanatotrimethylsilane (85% pure, 40.0 mL, 0.30 mol). The source for isocyanatotrimethylsilane is TCI. After the addition, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature over 1 h. The reaction mixture was quenched with acetic acid (40 g, 0.67 mol) and 200 mL of water. The mixture was allowed to stir overnight and the white solid that formed was collected through filtration and washed with water. The filtrate was extracted with ethyl acetate (3×300 mL). The solid that was collected previously was dissolved in the combined organic layers, and the resulting solution was washed with brine (2×200 mL), dried over MgSO4 and concentrated in vacuo. The residue was suspended in 200 mL of diethyl ether and sonicated. The remaining solid was collected through filtration and washed with minimum amount of diethyl ether to provide 3,4-dichloropicolinamide (14.8 g, 39%). | |
39.6% | The compound tetramethylpiperazine (311 mg, 2.2 mmol) was dissolved in 8 ml of anhydrous ether,Then at 0 CN-Butyllithium (138 mg, 2.2 mmol) was added dropwise,And stirred under ice bath for 30 min.The reaction temperature was then lowered to -78 C for 30 min,While <strong>[55934-00-4]3,4-dichloropyridine</strong> (296 mg, 2 mmol) was dissolved in 2 ml of anhydrous ether dropwise to the reaction,The reaction was carried out at -78 C for 2 hours,Reaction is completed,Trimethylsilyl isocyanate (400 ul, 3 mmol) was added to room temperature for 1 h.After completion of the reaction, add 50ml of acetic acid: water (1: 4) solution. Stirred overnight, extracted with ethyl acetate,Saturated sodium bicarbonate, and saturated brine to give a brown oil,The pink powder 1f (150 mg, 39.6%) was obtained by column chromatography (methanol: dichloromethane = 1: 100 to 1:30). | |
34% | Step 2) 3,4-dichloropicolinamide [0172] To a mixture of 2,2,6,6-tetramethylpiperidine (6.2 mL, 37.2 mmol) in diethylether (50 mL) was added w-BuLi in hexane (2.5M, 23 mL, 57.5 mmol) at 0 C via syringe over 15 min. The mixture was stirred at 0 C for 0.5 hour, then cooled to -78 C. A solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (5.00 g, 33.8 mmol) in diethylether (20 mL) was added to the mixture via a syringe over 15 minutes. The reaction was stirred at -78 C for 2 hours, then isocyanatotrimethylsilane (94 % pure, 6.7 mL, 50.7 mmol) was added. The mixture was warmed up to rt and further stirred for 2 hours, quenched with acetic acid (6.76 g, 112.6 mmol) in 35 mL of water. The mixture was further stirred overnight. The titled product was precipitated overnight as a white solid, which was collected through filtration. More products were recovered from the filtrate. Thus, the filtrate was extracted with ethyl acetate (50 mL x 3) and the combined organic phases were washed with brine (50 mL), dried over anhydrous a2S04, and concentrated in vacuo. The solid was combined and washed with 35 mL of Et20 to give the title compound as a pale yellow solid (2.20 g, 34.0%). MS (ESI, pos. ion) m/z: 191.1 [M+H]+; NMR (400 MHz, DMSO-i): delta (ppm) 8.48 (d, J= 5.2 Hz, 1H), 8.09 (br s, 1H), 7.82 (s, 1H), 7.81 (d, J= 5.2 Hz, 1H). | |
34% | Step 2) 3,4-dichloropicolinamide To a mixture of 2,2,6,6-tetramethylpiperidine (6.2 mL, 37.2 mmol) in diethylether (50 mL) was added n-BuLi in hexane (2.5M, 23 mL, 57.5 mmol) at 0 C. via syringe over 15 min. The mixture was stirred at 0 C. for 0.5 hour, then cooled to -78 C. A solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (5.00 g, 33 8 mmol) in diethylether (20 mL) was added to the mixture via a syringe over 15 minutes. The reaction was stirred at -78 C. for 2 hours, then isocyanatotrimethylsilane (94% pure, 6.7 mL, 50.7 mmol) was added. The mixture was warmed up to rt and further stirred for 2 hours, quenched with acetic acid (6.76 g, 112.6 mmol) in 35 mL of water. The mixture was further stirred overnight. The titled product was precipitated overnight as a white solid, which was collected through filtration. More products were recovered from the filtrate. Thus, the filtrate was extracted with ethyl acetate (50 mL*3) and the combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The solid was combined and washed with 35 mL of Et2O to give the title compound as a pale yellow solid (2.20 g, 34.0%). MS (ESI, pos. ion) m/z: 191.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta (ppm) 8.48 (d, J=5.2 Hz, 1H), 8.09 (br s, 1H), 7.82 (s, 1H), 7.81 (d, J=5.2 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | As described previously by Marzi, E. et al. (Eur. J. Org. Chem. 2001, 1371-1376), 2,2,6,6-tetramethylpiperidine (8.84 mL, 52 mmol, Aldrich) in 50 mL of ether at 0 C. was charged with n-BuLi (33 mL, 52 mmol, Aldrich, 1.6 M hexanes). After stirring at 0 C. for 30 min, the solution was cooled to -78 C. and charged with a solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (7.0 g, 47 mmol, Matrix) in 5 mL of ether. After stirring at -78 C. for 2 h, carbon dioxide (dry ice) was bubbled into the reaction mixture via cannula at which time the solution became heterogeneous. After bubbling carbon dioxide into the reaction at -78 C. for 10 min, the cooling bath was removed and the reaction mixture was allowed to warm to rt with CO2 bubbling. The reaction was quenched with saturated aqueous ammonium chloride solution (50 mL) and stirred at rt under an atmosphere of air for 5 min. The reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (2×75 mL) to remove any remaining starting material. The aqueous layer was acidified to pH 1-2 with 1N aqueous HCl solution and extracted with ethyl acetate (2×100 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo to give 3,4-dichloropicolinic acid (3.5 g, 39%) as a yellow solid. 1H NMR (DMSO-d6) delta 8.53 (d, 1H, J=5.2 Hz), 7.90 (d, 1H, J=5.2 Hz); MS (ESI+) m/z 192.08 (M+H)+. | |
2.90 g | Take a 250ml reaction bottle, add 8.84ml of 2,2,6,6-tetramethylpiperidine, 50ml of ether, lower the temperature to 0 C, dropwise add 33ml of 1.6M n-butyllithium-hexane solution, and stir for 30min. Continue to lower the temperature to -78 C, dropwise add 7.0g of <strong>[55934-00-4]3,4-dichloropyridine</strong> / 5ml ether solution, keep the reaction for 2.0h, and continuously introduce carbon dioxide gas into the reaction solution for 0.5h. The temperature was naturally raised to room temperature in a carbon dioxide atmosphere. After the reaction was completed, 50 ml of saturated ammonium chloride was added to quench the reaction. Add 150ml of water, 75ml * 2 ethyl acetate to extract impurities, keep the aqueous phase, adjust the pH to 1.0-2.0 with 1N dilute hydrochloric acid, It was extracted with 100 ml * 2 ethyl acetate, and the organic phases were combined, dried, and concentrated to dryness under reduced pressure to obtain 2.90 g of compound I-39-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In a round-bottom flask, equipped with a stirrer, thermometer and reflux condenser, mix under nitrogen in the specified order: 200 mL of dry THF and 12.308 g (0.12 mol) of diisopropylamine. Cool the resulting mixture to -40 ; add, dropwise, 48.7 mL of 2.5M butyllithium in hexane. Allow the mixture to stand at this temperature. After 30 minutes, cool the mixture to -78 ; add, dropwise, solution of 15.7 g (0.068 mol) of BCD-BTK-30-7 in 100 mL of dry THF. After that, allow the reaction mass to stand for 2.5 hours. Add 15 g (0.2 mol) of DMF, maintaining the temperature at -78 . Stop the cooling and allow the reaction mixture to warm to room temperature. Allow to stand for another hour. Add, while cooling the reaction mixture, 30 mL of methanol and 150 mL of NH4Cl aqueous solution. Allow to stand for 30 minutes. To the reaction mass add 1000 mL of water, 500 mL of dichloromethane, and transfer the emulsion to a separatory funnel. Separate the organic layer; re-extract the aqueous layer using 200 mL of dichloromethane. Combine the organic layers, wash with water, and dry with sodium sulfate. Distill off dichloromethane. Yield: 17 g (96%). | |
67% | Method 2:Example 30:3,5-Dichloro-4-[7-chloro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrikStep l :4,5-Dichloropyridine-3-carbaldehydeTo a solution of diisopropylamine (9.7 mL, 69.1 mmol) in THF (60 mL) at -30 C was added «-butyllithium (2.5 M in hexanes, 27.6 mL, 69.1 mmol). The reaction mixture was stirred for 15 minutes then cooled to -78 C. A solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (8.53 g, 57.6 mmol) in THF (20 mL) was added dropwise over 20 minutes then the mixture was stirred at -78 C for 2.5 hours. DMF (5.4 mL, 69.1 mmol) was added and the reaction was warmed to room temperature. The reaction mixture was quenched with ammonium chloride (sat. aq., 300 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in pentane) to afford the title compound as a white solid (6.78 g, 67% yield). NMR (400 MHz, CDC13): delta 10.49 (s, 1H), 8.92 (s, 1H), 8.82 (s, 1H). | |
63% | To a solution of diisopropylamine (10.73 ml, 75.9 mmol) in THF (60 ml) at -4OC, was added n-butyllithium (47.45 ml, 75.9 mmol, 1.6M in hexanes) and the solution was stirred for 15 min at -4OC, before cooling to -7OC. A solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (10.7 g, 72.3 mmol) in THF (30 ml) was added dropwise to maintain the temperature below -65C. The reaction was stirred at -7OC for 2 hours before the addition of DMF (6.74 ml, 86.8 mmol). The reaction was then stirred at -4OC for 1 hoursand then allowed to warm to -5C before the careful addition of saturated ammonium chloride solution (50 ml) with rapid stirring over 3 min. The mixture was then partitioned between saturated ammonium chloride (150 ml) and dichloromethane (150 ml) and the layers separated. The aqueous layer was extracted with dichloromethane (2 x 100 ml) and the combined organic layers were dried over magnesium sulfate, then concentrated in vacuo. Purification of the resultant residue by flash chromatography (Si- PPC, dichloromethane : ethyl acetate gradient 100:0 to 94:6) afforded the title compound as white waxy solid (8.01 g, 63%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.1% | With potassium tert-butylate; In tetrahydrofuran; at 20℃; | Example 1.20: Preparation of 5-(4-((lr,4r)-4-(3-Chloropyridin-4- yloxy)cyclohexyloxy)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole (Compound 20).To a solution of (lr,4r)-4-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4- yloxy)cyclohexanol (132 mg, 0.427 mmol) and <strong>[55934-00-4]3,4-dichloropyridine</strong> (71 mg, 0.480 mmol) THF (1 mL), 1 M potassium 2-methylpropan-2-olate in THF (0.6 mL, 0.600 mmol) was added. After stirring at room temperature over night, the mixture was extracted with water and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography (Si02, hexane/AcOEt gradient). Proper fractions were concentrated and the residue was re -purified by HPLC (CH3CN/H20 gradient + 0.1 % TFA). Proper fractions were partly concentrated and the residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give the title compound (160 mg, 0.380 mmol, 89.1 %) as a white solid. LCMS m/z = 421.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.31 (d, J = 7.8 Hz, 6H), 1.52-1.61 (m ,2H), 1.67-1.77 (m, 4H), 1.87-1.94 (m, 2H), 1.99-2.06 (m, 2H), 2.09-2.16 (m, 2H), 2.87-2.94 (m, 1H), 3.44-3.51 (m, 2H), 3.62-3.71 (m, 2H), 3.82-3.89 (m, 2H), 4.54-4.57 (m, 1H), 6.84 (d, J = 5.6 Hz, 1H), 8.36 (d, J = 5.6 Hz, 1H), 8.48 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 90 - 100℃; for 2h; | General procedure: 3.9 Preparation of Compound 3 A mixture of compound 1 (1.5 g, 10 mmol) and compound 2 (5.0 g, 50 mmol) was heated to 90-100 C. for 2 h. The mixture was diluted with DCM (250 mL) and washed with NH4Cl (50 mL×2). The combined organic layer was concentrated to give the crude product, which was used in next step directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.6% | To a solution of diisopropylamine (2.1 mL, 15.1 mmol, 1.1 eq) in dry THF (24 mL) at- 78C was added a 2.5M BuLi solution in hexane (8.2 mL, 20.0 mmol,1.3eq). The mixture was allowed to warm to 0 C and stirred around 1 h. After this time the solution was cooled to- 78C and <strong>[55934-00-4]3,4-dichloropyridine</strong> (2.0 g, 13.7 mmol,leq) inS mL of dry THF was added. The reaction mixture was stirred for additional 4 h, and then the corresponding 4-(2-fluoro-3- methoxyphenoxy)benzaldehyde (3.36 g, 13.7 mmol, leq) was added and the mixture was stirred and allowed to warm to room temperature during overnight. Excess of LDA was destroyed with H20 (25 mL), and the mixture extracted with Et20 (3x50 mL). The organicphases were combined, dried over Na2504, volatile components were removed under vacuumand the residue was purified by column chromatography on silica gel (gradient: DCMIMeOH= 200:1 - 50/ 1)to give the title product (4.5 g, yield 83.6%). HNMR (400 MHz, CDC13):o 8.78 (s, 1H), 8.55 (s,1H), 7.30 (d, J= 8.0 Hz, 2H), 7.02(d, J= 8.0 Hz, 2H),6.98-6.66 (m,3H), 6.12 (s, 1H), 3.93(s, 3H). LCMS: m/z = 394.1 [M+Hf |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.72 g | In a three-necked bottle with a nitrogen protection device,Input6-trifluoromethyl hydrazine(2.00g, 10.8mmol),20 mL of N,N-dimethylacetamide, stirring to reduce the temperature to below 0 C, adding 60% sodium hydrogen (0.48 g, 11.9 mmol), and stirring for 0.5 hour.Add dropwise4,6-dichloropyrimidine(1.45 g, 9.8 mmol) in N,N-dimethylacetamide (20 mL),After the addition, the temperature is raised to 60 C.Stir the reaction for 8 hours,Add 50mL of water,Ethyl acetate extraction (100 mL),The organic phase is washed with brine,Dry over anhydrous sodium sulfate,Concentrate to dryness under reduced pressure.The concentrate was purified by silica gel chromatography.get1-(3-chloropyridin-4-yl)-<strong>[13544-43-9]6-trifluoromethyl-1H-indole</strong>(Intermediate 1-a) (1.72 g). |
Yield | Reaction Conditions | Operation in experiment |
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With n-butyllithium; | Example 33 Synthesis of 3,4-dichloropicolinamide. To a solution of 2,2,6,6-tetramethylpiperidine (5.2 g, 37.2 mmol) in diethyl ether (80 mL) at 0 C. was added n-BuLi (2.4 M, 15.5 mL, 37.2 mmol) dropwise. The resulting solution was stirred at 0 C. for 0.5 h and at -78 C. for 0.5 h. To this mixture was then slowly added a solution of <strong>[55934-00-4]3,4-dichloropyridine</strong> (5 g, 33.8 mmol) in diethyl ether (10 mL) dropwise. The resulting mixture was stirred at -78 C. for 2 h before the addition of isocyanotrimethylsilane (5.83 g, 50.7 mmol). After the addition, the cooling bath was removed and the reaction mixture was allowed to warm to RT over 1 h. The reaction mixture was stirred at 25 C. for 16 h, H2O (100 mL) was added, extracted with ethyl acetate (100 mL*3), washed with brine (30 mL), dried over MgSO4 and concentrated in vacuo. The residue was suspended in 20 mL of diethyl ether and sonicated. The solid was collected through filtration and washed with minimum amount of diethyl ether to give 3,4-dichloropicolinamide (2.3 g, yield: 35%) as a yellow solid. ESI-MS [M+H]+: 191.1. |
Tags: 55934-00-4 synthesis path| 55934-00-4 SDS| 55934-00-4 COA| 55934-00-4 purity| 55934-00-4 application| 55934-00-4 NMR| 55934-00-4 COA| 55934-00-4 structure
[ 7379-35-3 ]
4-Chloropyridine hydrochloride
Similarity: 0.85
[ 7379-35-3 ]
4-Chloropyridine hydrochloride
Similarity: 0.85
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