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CAS No. : | 122918-25-6 | MDL No. : | MFCD00234142 |
Formula : | C6H3BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HNEBPTAKURBYRM-UHFFFAOYSA-N |
M.W : | 183.01 | Pubchem ID : | 15100859 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.65 |
TPSA : | 36.68 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) : | -6.05 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 1.93 |
Log Po/w (WLOGP) : | 1.72 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 2.02 |
Consensus Log Po/w : | 1.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.68 |
Solubility : | 0.379 mg/ml ; 0.00207 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.32 |
Solubility : | 0.867 mg/ml ; 0.00474 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.96 |
Solubility : | 0.199 mg/ml ; 0.00109 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.04 |
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 |
---|---|---|
69% | With manganese; zirconocene dichloride; (Me)2Dipyr(H)2*NiCl2; lithium chloride In 1,2-dimethoxyethane at 20℃; for 19 h; Inert atmosphere | General procedure: To a suspension of a NiCl2-complex (0.01 mmol, 0.02 equiv), Zr(cp)2Cl2 (Strem, 99percent; 7.3 mg, 0.025 mmol, 0.05 equiv), Mn powder (Aldrich, 99.99percent; 54.9 mg, 1.0 mmol, 2.0 equiv) and LiCl (Aldrich, anhydrous, ground powder; 42.4 mg, 1.0 mmol, 2.0 equiv) in DME (Aldrich, anhydrous, 99.5percent; 1.0 mL) was added an iodide (0.5 mmol) under nitrogen. The mixture was stirred at rt under nitrogen until the reaction completed (TLC). Except for the dipyridyls, the mixture was loaded on silica gel directly, and the flash chromatography on silica gel gave the homo-coupling product. For dipyridyls, the reaction was quenched with aq. NH4OH (27percent w/w, 0.6 mL), stirred for 10 min, extracted with CH2Cl2 (10 mL .x. 3), washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give the homocoupling product. For alkenyl halide substrates (Fig. 3 and Table 3), the reaction was done in 0.2 mmol scale (C: 0.5 M) with added toluene (42 μl, 0.4 mmol, 2.0 equiv) as an internal standard. After the reaction was completed, a small portion (50 μL) of the mixture was passed through a small silica pad, and eluted with CDCl3 (1 mL). The yield was estimated from 1H NMR (600 MHz, CDCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With caesium carbonate;palladium diacetate; johnphos; In toluene; at 130℃; for 96h; | a) 6-[(1-Methylpiperidin-4-yl)oxy]pyridine-2-carbonitrile 1-Methylpiperidin-4-ol (1.89 g, 0.0164 mol), <strong>[122918-25-6]6-bromo-2-pyridinecarbonitrile</strong> (3.00 g, 0.0164 mol), Pd(OAc)2 (0.184 g, 0.820 mmol), 2-(di-t-butylphosphino)biphenyl (0.303 g, 1.02 mmol) and Cs(CO3)2 were mixed in 100 mL of toluene. The reaction mixture was stirred under argon and heated to 130 C. in an oil bath for 4 days. The reaction mixture was diluted with EtOAc and washed with water, dried over Na2SO4 and evaporated. The crude product was flash chromatographed on silica gel DCM/MeOH/TEA 95/5/1 to give 1.62 g (45%) of the desired product. 1H NMR (500 MHz, CDCl3) delta 7.67 (m, 1H), 7.29 (d, 1H), 6.95 (d, 1H), 5.12 (m, 1H), 2.74 (m, 2H), 2.40-2.30 (m, 5H, thereof a singlet at 2.35), 2.09 (m, 2H), 1.86 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With caesium carbonate;palladium diacetate; johnphos; In toluene; at 130℃; for 24h; | a) tert-Butyl 4-[(6-cyanopyridin-2-yl)oxy]piperidine-1-carboxylate 6-Bromo-2-pyridinecarbonitrile (1.00 g, 5.46 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (1.10 g, 5.46 mmol), Pd(OAc)2 (61 mg, 0.27 mmol), 2-(di-t-butylphosphino)biphenyl (98 mg, 0.328 mmol) and Cs2(CO3) (3.56 g, 10.93 mmol) were mixed in toluene (20 ml). The reaction was stirred under an N2 atmosphere and heated to 130 C. on an oil bath for 24 h. The solvent was evaporated in vacuo and the remaining separated between EtOAc (500 ml) and water (500 ml). The aqueous phase was extracted with EtOAc (500 ml). The combined organic phases were washed with water (500 ml), dried with Na2SO4 (s), filtered and evaporated in vacuo. Purification by silica gel flash chromatography using a 40 g Biotage column with a gradient of 5-30% EtOAc in heptane giving the title compound as a white solid. Yield: 605 mg (37%). 1H NMR (400 MHz, CDCl3) delta 7.63 (dd, 1H, J=8.4 Hz, J=7.3 Hz), 7.25 (d, 1H, J=7.3 Hz), 6.90 (d, 1H, J=8.4 Hz), 5.21 (m, 1H), 3.74 (m, 2H), 3.25 (m, 2H), 1.95 (m, 2H), 1.68 (m, 2H), 1.44 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | WORKING EXAMPLE 3 Production of 6-bromo-2-cyanopyridine n-Butylmagnesium chloride (3.49 mmol) in 2.05M tetrahydrofuran solution (1.70 mL) was added to ice-cooled n-butyllithium (7.03 mmol) in 1.45M hexane (4.85 mL). The mixture was stirred at 0 C. for 15 minutes, and cooled to -10 C. to give a suspension. 2,6-Dibromopyridine (2.37 g, 10 mmol) in toluene (25 mL) was added to the suspension below -5 C. over a period of 10 minutes or more. The mixture was stirred at -10 C. for 3 hours, and p-toluenesulfonyl cyanide (2.48 g, 13.3 mmol) was added. After the mixture was stirred at 0 C. for 30 minutes, an aqueous solution (15 mL) of 1M acetic acid was added thereto. The reaction mixture was extracted twice with ethyl acetate (50 mL). The organic extracts combined were washed with an aqueous saturated solution (15 mL) of sodium chloride, dried over magnesium sulfate, and purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (10:1, v/v) to give the title compound (942 mg, about 51% yield) as orange powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; triethylamine; In methanol; at 20℃; for 15h; | General procedure: To a solution of3(11.7 mmol) in MeOH (20 mL) was added hydroxylamine hydrochloride (1.0 g, 14.0 mmol) and triethylamine (3.5 g, 35.1 mmol). The mixture was stirred at room temperature for 15 h. MeOH was removed in vacuo. The residue was added water and extracted with ethyl acetate (330 mL), washed with brine (330 mL), dried over anhydrous Na2SO4and concentrated. The residue was subjected to silica gel chromatography with petroleum ether/EtOAc (4:1) to give4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 80℃; | Example 1-52 6'-([(Trans)-2-oxo-3-(3-pyridazinyl)-1-oxa-3-azaspiro[4.5]dec-8-yl]methyl}amino)-2,3'-bipyridine-6-carbonitrile dihydrochloride PdCl2(dppf)-CH2Cl2 adduct (64.4 mg, 0.079 mmol) and aqueous 2.0M sodium carbonate (0.394 ml, 0.788 mmol) were added to a mixture of <strong>[122918-25-6]6-bromo-2-pyridinecarbonitrile</strong> (87 mg, 0.473 mmol) and [6-([(trans)-2-oxo-3-(3-pyridazinyl)-1-oxa-3-azaspiro[4.5]dec-8-yl]methyl}amino)-3-pyridinyl]boronic acid (Intermediate 111, 151 mg, 0.394 mmol) in dry DMF (3 ml) and the resulting mixture was shaken at 80 C. overnight. Additional 2.0M aq sodium carbonate (0.394 ml, 0.788 mmol), PdCl2(dppf)-CH2Cl2 adduct (64.4 mg, 0.079 mmol) and <strong>[122918-25-6]6-bromo-2-pyridinecarbonitrile</strong> (87 mg, 0.473 mmol) were added and the mixture was shaken at 80 C. for further 6 hours then it was cooled down, filtered through IST filter tube and concentrated in vacuo to give a brown residue. The residue was dissolved in MeOHDCM, loaded into SCX cartridge (5 g), washed with MeOH and eluted with 2.0M NH3 in MeOH. After concentration in vacuo, the resulting crude was purified by RP-flash chromatography (SNAP C18 60 g column) eluding in gradient with 0% phase B (acetonitrile) (2 cv), 0%-50% phase Bphase A (H2O+5% acetonitrile+0.1% HCO2H) (in 12 cv), 50% phase B (lcv), 50%-95% phase B (in 6 cv), 95% phase B (1 cv) then 95%-0% phase B (in 2 cv) to afford a residue. The residue was loaded onto SCX cartridge, washed with methanol and eluted with 2.0M NH3 in MeOH to obtain 6'-([(trans)-2-oxo-3-(3-pyridazinyl)-1-oxa-3-azaspiro[4.5]dec-8-yl]methyl}amino)-2,3'-bipyridine-6-carbonitrile as a yellowish solid (46 mg, 0.104 mmol, 26%). 1H NMR (400 MHz, CDCl3): delta 1.18-1.38 (m, 2H), 1.72-1.99 (m, 3H), 1.99-2.12 (m, 4H), 3.29-3.40 (t, 2H), 4.23 (s, 2H), 4.86-4.99 (m, 1H), 6.48-6.57 (d, 1H), 7.47-7.59 (m, 2H), 7.77-7.91 (m, 2H), 8.15-8.25 (m, 1H), 8.54-8.62 (m, 1H), 8.69-8.76 (m, 1H), 8.92-9.01 (m, 1H); UPLCMS: 0.75 min, mass 442 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(l) iodide; potassium carbonate; 1,1,3,3-tetramethyl-1,3-bis(3-pyridinyl)disiloxane; In N,N-dimethyl-formamide; at 100℃; for 24h;Inert atmosphere; | General procedure: Aryl iodide or bromides (1 mmol), ArOH (1 mmol), CuI(20 mol%), and dimethyl di (2-pyridyl)silane (20 mol%) were placed in a small round-bottom flask. DMF (3 mL) and K2CO3(276 mg, 2 mmol) were then added together. The mixture was stirred for 24 h at 100C in nitrogen atmosphere. The reaction mixture was cooled to room temperature. Ethyl acetate(10 mL) and H2O (1 mL) were added and the mixture was stirred. The organic layer was separated and the aqueous layer was extracted twice more with ethyl acetate (10 mL). Combined organic layer was dried overNa2SO4 and filtered. The filtrate was concentrated and the resulting residue was purified by silica gelchromatography and afforded the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With manganese; zirconocene dichloride; (Me)2Dipyr(H)2*NiCl2; lithium chloride; In 1,2-dimethoxyethane; at 20℃; for 19h;Inert atmosphere; | General procedure: To a suspension of a NiCl2-complex (0.01 mmol, 0.02 equiv), Zr(cp)2Cl2 (Strem, 99%; 7.3 mg, 0.025 mmol, 0.05 equiv), Mn powder (Aldrich, 99.99%; 54.9 mg, 1.0 mmol, 2.0 equiv) and LiCl (Aldrich, anhydrous, ground powder; 42.4 mg, 1.0 mmol, 2.0 equiv) in DME (Aldrich, anhydrous, 99.5%; 1.0 mL) was added an iodide (0.5 mmol) under nitrogen. The mixture was stirred at rt under nitrogen until the reaction completed (TLC). Except for the dipyridyls, the mixture was loaded on silica gel directly, and the flash chromatography on silica gel gave the homo-coupling product. For dipyridyls, the reaction was quenched with aq. NH4OH (27% w/w, 0.6 mL), stirred for 10 min, extracted with CH2Cl2 (10 mL × 3), washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give the homocoupling product. For alkenyl halide substrates (Fig. 3 and Table 3), the reaction was done in 0.2 mmol scale (C: 0.5 M) with added toluene (42 mul, 0.4 mmol, 2.0 equiv) as an internal standard. After the reaction was completed, a small portion (50 muL) of the mixture was passed through a small silica pad, and eluted with CDCl3 (1 mL). The yield was estimated from 1H NMR (600 MHz, CDCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 15h;Inert atmosphere; | General procedure for coupling reaction: An oven-dried resealable Schlenk tube were charged with Pd(OAc)2 (6.7 mg, 0.03 mmol), Xantphos (34.7 mg, 0.06 mmol), 2-methylpropane-2-sulfinamide (145 mg, 1.2 mmol) and Cs2CO3 (650 mg, 2.0 mmol). The Schlenk tube was evacuated and back-filled with argon. 4-bromo-2-methylbenzonitrile (196 mg, 1.0 mmol) and dioxane (3 ml) were added and the Schlenk tube was then sealed with a Teflon screw cap and placed in a preheated oil bath at 100oC for 15 h. After cooling of the reaction mixture to room temperature, water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by flash chromatography. Yield: 228 mg, 97 % [table-1, entry-5]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃; for 16h; | Preparation of 6-{3-ri-(6-methyl-pyridin-2-yl)-eth-(E)-ylideneaminooxy1-prop-l-ynyl>- pyridine-2-carbonitrile2-Bromo-6-cyanopyridin (1.57 g) and E-l-(6-methyl-pyridin-2-yl)-ethanone O-prop-2- ynyl-oxime (1.62 g) were dissolved in THF (40 ml_). Diisopropylamine (2.42 ml_),dichlorobis(triphenylphospine) palladium(II) (181 mg) and copper(I) iodide (131 mg) were added. After stirring for 16h at ambient temperature the reaction mixture was diluted with ethyl acetate washed with sodium bicarbonate (10% aqueous solution) and brine. The organic phase was dried over sodium sulfate, concentrated and purified by chromatography over silica to give a pink solid (1.95 g). ^-NMR (CDCI3, 400 MHz):7.80 (t, IH), 7.71 (d, IH), 7.63 (m, 2H), 7.56 (t, IH), 7.12 (d, IH), 5.08 (s, 2H), 2.58 (s, 3H), 2.48 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; In tetrahydrofuran; at 25℃; for 2h;Inert atmosphere; | In this example, the reactivity of the solid zinc reagents towards palladium-catalyzed Negxs/zz'-cross-coupling reactions is demonstrated.In a dry and argon-flushed 25 mL Schlenk-flask, equipped with a magnetic stirring bar and a septum, 3-(trifluoromethyl)phenylzinc pivalate (Id prepared above; 780 mg,882 mg/mmol, 0.88 mmol) is dissolved in dry THF (1.8 mL). 6-Bromopyridine-2-carbonitrile (5e; 135 mg, 0.74 mmol) and PEPPSI-zPr (14 mg, 0.02 mmol) are added and the mixture is stirred for 2 h at 25 C. Saturated aqueous H4CI (10 mL) is added and the aqueous layer is extracted with diethyl ether (3 x 15 mL). The combined organic layers are dried over sodium sulfate and the solvent is removed in vacuo.Purification by flash chromatography (silica gel, pentane/Et20 = 1 : 1) affords 6-[3- (trifluoromethyl)phenyl]pyridine-2-carbonitrile (6f; 144 mg, 0.58 mmol, 78 %) as a colourless solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tris-(o-tolyl)phosphine;palladium dichloride; In N,N-dimethyl-formamide; at 20 - 130℃;Inert atmosphere; | Under argon, 3-fluoro-5-(1,3-thiazol-2-yl)pyridine (0.99 g, 5.47 mmol) and <strong>[122918-25-6]6-bromopyridin-2-carbonitrile</strong> (1.0 g, 5.47 mmol) were initially charged in DMF (15 ml). After 10 min, at room temperature, tris(2-methylphenyl)phosphine (0.13 g, 0.23 mmol) and palladium(II) chloride (0.1 g, 0.55 mmol) were added. The reaction mixture was stirred at 130 C. for 14 h. After cooling, water and ethyl acetate were added and the precipitated product was filtered off with suction. The organic phase of the filtrate was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and the solvent was removed under reduced pressure. The residue was stirred with dichloromethane and filtered off with suction. This gave a total of 0.94 g (61% of theory) of 6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbonitrile.HPLC-MS: LogP(HCOOH): 2.51; mass (m/z): 283 (M+H)+ 1H NMR (d6-DMSO): 8.02 (d, 1H), 8.20 (t, 1H), 8.32-8.46 (m, 1H), 8.44 (d, 1H), 8.75 (d, 1H), 8.84 (s, 1H), 9.12 (s, 1H) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 85℃; for 3h;Inert atmosphere; | General procedure: To a solution of 2-ethynylquinoline 9 (50 mg, 0.33 mmol) in triethylamine (0.4 mL) was added PdCl2(PPh3)2 (12 mg, 0.02 mmol), copper(I) iodide 98% (6 mg, 0.03 mmol) and 2- bromo-3-trifluoromethylpyridine (110 mg, 0.5 mmol). After the reaction was stirred at 85 C for 3 h, it was allowed to cool to room temperature and filtered through a pad of Celite by the aid of EtOAc. The filtrate was treated with water and extracted with EtOAc (3 x 10 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/hexane = 1:1) to give 2-((3-(trifluoromethyl)pyridin-2-yl)ethynyl) quinoline 6a (48 mg, 49%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 6h;Reflux; Inert atmosphere; | <strong>[122918-25-6]2-bromo-6-cyanopyridine</strong> (424 mg, 2.3 mmol), 4-(trifluoromethyl)phenylboronic acid (440 mg, 2.3 mmol) and Pd (PPh3)4 (134 mg, 0.12 mmol) were added in a 100 ml single neck bottle, followed by adding THF (30 ml) and a potassium carbonate solution (potassium carbonate (0.96 g) in deionized water (7 ml)) to obtain a mixture. The mixture was heated under reflux for 6 hours under a nitrogen gas atmosphere. After the reaction was finished, the mixture was cooled to room temperature, followed by removing solvent by virtue of reduced pressure distillation to obtain a distilled mixture. Then, the distilled mixture was added with dichloromethane and water for extraction. The dichloromethane layer was collected and added with magnesium sulfate to remove water. The dichloromethane layer was then filtrated and the filtrate was collected. Next, the filtrate was concentrated by means of reduced pressure distillation to obtain a yellow crude product. The resultant yellow crude product was subjected to column chromatography, in which a mixture of ethyl acetate and hexane(ethyl acetate: hexane=1:4) was used as an eluent. An eluate was collected followed by removing the eluent using a rotary evaporator. A white solid product was obtained (460 mg, 1.9 mmol, 80% yield).The spectrum analysis for the white solid product is: 1H NMR (400 MHz, CDCl3, 298K), delta(ppm): 8.14 (d, JHH=8.0 Hz, 2H), 8.02?7.90 (m, 2H), 7.75 (d, JHH=8.0 Hz, 2H), 7.68 (d, JHH=7.2 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux; Inert atmosphere; | 2-bromo-6-cyanopyridine (0.50 g, 2.7 mmol), the colorless oily liquid of the preparation 1 (0.89 g, 3.3 mmol) and Pd(PPh3)4 (158 mg, 0.14 mmol) were added into a 100 ml single neck bottle, followed by adding THF (30 ml) and a potassium carbonate solution (potassium carbonate (0.94 g) in deionized water (7 ml)) to obtain a mixture. The mixture was heated under reflux for 4 hours under a nitrogen gas atmosphere. After the reaction was finished, the mixture was cooled to room temperature, followed by solvent removal by virtue of reduced pressure distillation to obtain a distilled mixture. Then, the distilled mixture was added with dichloromethane and water for extraction. The dichloromethane layer was collected and added with magnesium sulfate to remove water. The dichloromethane layer was then filtrated and the filtrate was collected. Next, the filtrate was concentrated by means of reduced pressure distillation to obtain a yellow solid product. The yellow solid product was subjected to column chromatography, in which a mixture of ethyl acetate and hexane(ethyl acetate: hexane=1:4) was used as an eluent. An eluate was collected followed by removing the eluent using a rotary evaporator. A white solid product was obtained (608 mg, 2.4 mmol, 90% yield. The spectrum analysis for the white solid product is: 1H NMR (400 MHz, CDCl3, 298K). delta(ppm): 8.27 (s, 1H), 8.22 (d, JHH=8.0 Hz, 1H), 8.02?7.90 (m, 2H), 7.76 ?7.59 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Reflux; Inert atmosphere; | <strong>[122918-25-6]2-bromo-6-cyanopyridine</strong> (1.10 g, 6.0 mmol), the colorless oily liquid of Preparation 2 (2 g, 6.9 mmol) and Pd(PPh3)4 (346 mg, 0.30 mmol) were added in a 100 ml single neck bottle, followed by adding THF (30 ml) and a potassium carbonate solution (potassium carbonate (2.07 g) in deionized water (7 ml)) to obtain a mixture. The mixture was heated under reflux for 5 hours under a nitrogen gas atmosphere. After the reaction was finished, the mixture was cooled to room temperature, followed by solvent removal by virtue of reduced pressure distillation to obtain a distilled mixture. Then, the distilled mixture was added with dichloromethane and water for extraction. The dichloromethane layer was collected and added with magnesium sulfate to remove water. Filtration was conducted after water was removed and a filtrate was collected. Next, the filtrate was concentrated by means of reduced pressure distillation to obtain a yellow solid product. The yellow solid product was subjected to column chromatography, in which a mixture of ethyl acetate and hexane(ethyl acetate: hexane=1:4) was used as an eluent. An eluate was collected followed by removing the eluent using a rotary evaporator. A white solid product was obtained (983 mg, 3.7 mmo, 61% yield).The spectrum analysis for the white solid product is: 1H NMR (400 MHz, CDCl3, 298K), delta(ppm): 8.30?8.21 (m, 2H), 7.96?7.91 (m, 2H), 7.70?7.63 (m, 1H), 7.33 (t, JHF=9.2 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 2h;Inert atmosphere; | Step 1: Di-tert-butyl 2-bromo-5^6,6^7-tetrahydro-5H-spiro[enzo| ylcarbamate (0.1 g, 0.2 mmol) was dissolved in DMF (1 mL), bis(pinacolato)diboron (90 mg, 0.4 mmol), potassium acetate (59 mg, 0.6 mmol) and Pd(dppf)Cl2 (16 mg, 0.02 mmol) were added and the solution was degassed under a stream of nitrogen for 10 min. The reaction was heated for 15 min at 80 C. The mixture was cooled and an aromatic or heteroaromatic bromide or chloride (0.2 mmol) and aqueous Cs2C03 (0.15 mL, 3.7 M, 0.55 mmol) were added and the solution was degassed again under a stream of nitrogen for 10 min. Pd(dppf)Cl (16 mg, 0.02 mmol) was added and the solution was heated for 2 hr at 80 C. The reaction was then cooled and evaporated in vacuo to leave a residue that was used directly in the next step without further purification. Step 2: Di-tert-butyl protected intermediate from step 1 (0.2 mmol) was stirred in trifluoroacteic acid (2 mL) for 18 hr at room temperature. The reaction mixture was evaporated in vacuo to leave a residue that was purified using preparative HPLC to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.48 g | With bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 70℃; for 18h;Inert atmosphere; | Step a. To a solution of 6-bromopicolinonitrile (CAS Number 122918-25-6) (1.0 g, 5.46 mmol) in acetonitrile (10 ml) was added l-ethoxy-l-(tributylstannyl)ethylene (CAS Number 97674-02-7) (1.97 g, 5.46 mmol) at rt. The resulting reaction mixture was degassed for 10 min before addition of dichlorobis(triphenylphosphine)palladium(II) (0.19 g, 0.27 mmol) at rt. The reaction mixture was heated at 70C for 18 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 25 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (8% EtOAc in hexane) to yield 6-(l-ethoxyvinyl)picolinonitrile (0.48 g, 2.75 mmol). LCMS: Method C, 2.39 min, MS: ES+ 175.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 120℃; for 0.25h;Microwave irradiation; | To a solution of <strong>[122918-25-6]6-bromopyridine-2-carbonitrile</strong> (80 mg, 0.44 mmol) and 4-(morpholin-4-yl)-5-(4,4, 5, 5-tetramethyl- 1, 3,2-d ioxaborolan-2-yl )-7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (P2) (241 mg, 0.523 mmol) in1,4-dioxane (2.5 mL) and water (0.5 mL) was addedtetrakis(triphenylphosphine)palladium(0) (51 mg, 44 pmol) and sodium carbonate (140 mg, 1.32 mmol). The reaction mixture was heated at 120 C under microwave irradiation for 15 minutes, then diluted with water (30 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over sodium sulfate, filtered, and concentratedin vacuo; purification via preparative thin layer chromatography (Eluent: 1:1 petroleum ether ethyl acetate) afforded the product as a brown oil. Yield: 110 mg, 0.252 mmol, 57%. 1H NMR (400 MHz, CDCl3) 8.52 (s, 1H), 7.84-7.93 (m, 2H), 7.74 (s, 1H), 7.59 (dd, J=7.0, 1.2 Hz, 1H), 5.66 (s, 2H), 3.56-3.65 (m, 6H), 3.34-3.40 (m, 4H), 0.93 (dd, J8.3, 8.0 Hz, 2H), -0.05 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | At 0C under a N2 flow, NaH (3.28 g, 82 mmol) was added to a solution of B2 (7.32 g,71 mmol) in DMF (80 mL). The mixture was stirred at RT for 30 min and I3 (10 g,54.6 mmol) was added (exothermic) and the mixture was stirred at RT for 4h. A 10% aqueous solution of NaHCO3 (150 mL) and then brine (150 mL) were added. The resulting mixture was extracted with EtOAc (twice). The organic layer was dried over MgSO4, filtered and the solvent was evaporated. The residue was taken up in the minimum of AcOEt, the precipitate was filtered off and dried to give intermediate J3 (9.04 g, 81% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 130℃; for 1.5h;Microwave irradiation; | A solution of the compound (555 mg, 1.0 mmol) obtained in Example 16-5), 6-bromo-2-cyanopyridine (283 mg, 1.5 mmol), tetrakis(triphenylphosphine)palladium(0) (231 mg, 0.2 mmol), and potassium carbonate (276 mg, 2 mmol) in dimethoxyethane (4 mL) and water (1 mL) was stirred at 130C for 1.5 h under microwave irradiation. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, the mixture was extracted with dichloromethane, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (Isco Combiflash, 40 g, methanol:ethyl acetate = 0:100 to 20:80, gradient) to obtain the title compound (466 mg, 88%) as a light yellow oily substance. 1H-NMR (400 MHz, CDCl3) delta: 0.05 (3H, s), 0.07 (3H, s), 0.91 (9H, s), 1.19 (3H, s), 1.47-1.54 (2H, m), 1.61-1.70 (2H, m), 2.54 (1H, ddd, J = 15.6, 7.8, 2.4 Hz), 2.69 (1H, ddd, J = 15.6, 7.8, 2.0 Hz), 3.40 (2H, s), 3.51 (1H, d, J = 9.8 Hz), 3.55 (1H, d, J = 9.8 Hz), 4.07 (1H, ddd, J = 14.4, 7.8, 2.0 Hz), 4.31 (1H, ddd, J = 14.4, 7.8, 2.4 Hz), 7.20 (2H, d, J = 8.5 Hz), 7. 62 (1H, dd, J = 7.3, 1.5 Hz), 7.86-7.92 (2H, m), 7.96 (2H, d, J = 8.5 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | A solution of 2,4-dimethoxy-6-methylbenzoic acid (4, 3.0 g, 15.8 mmol) in THF (14 mL) was slowly added to a solution of n-BuLi (22.4 mL, 35.8 mmol), diisopropylamine (0.95 mL, 6.7 mmol) and THF (14 mL) at -78 C. After the addition, the solution was allowed to warm to 0 C. and stirred for 1 h. The solution was cooled to -78 C. and a solution of <strong>[122918-25-6]6-bromo-2-pyridinecarbonitrile</strong> (2.9 g, 15.8 mmol) and THF (14 mL) was added. The reaction mixture was allowed to warm to room temperature over 24 h and was quenched by the addition of water. The mixture was extracted with CH2Cl2 (3×100 mL) and the combined organic layers were dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (0-5% methanol in CH2Cl2) to provide the title compound as a brown solid (460 mg, 8%): 1H NMR (300 MHz, CDCl3) delta 9.77 (s, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.64 (t, J=7.8 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 6.93 (s, 1H), 6.56 (s, 1H), 6.51 (s, 1H), 3.99 (s, 3H), 3.91 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With Pd(Q-Phos)2; sodium t-butanolate; In toluene; at 50℃;Inert atmosphere; | In a flask were added I -((2S,3R,4R)-4-am ino-2-cyclopropyl-6-fluoro-3-methyl-3,4-dihyd roquinolin1(2H)-yl)ethanone (for a preparation see Intermediate 332, 150 mg, 0.572 mmol), 6-bromopicolinonitrile (157 mg, 0.858 mmol), sodium tert-butoxide (110 mg, 1.144 mmol) andPd(QPhos)2 (87 mg, 0.057 mmol) in toluene (4 mL). Reaction mixture was stirred under nitrogen at50 C for 3 h. A further portion of Pd(QPhos)2 (43.7 mg, 0.029 mmol) was added and reactionmixture left stirring at 50 C in the stirrer plate overnight. Reaction mixture was concentrated invacuo to afford 561.9mg of red gum crude. Resulting crude was purified by silica gelchromatography, 25 g column, 0-3 % 2M NH3 in MeOH in DCM gradient over 15 column volumes.Relevant fractions were combined and volatiles were removed under reduced pressure to afford 177mg of red gum. This compound was repurified by silica gel chromatography, (25 g column, 15-75 %EtOAc in cyclohexane over 20 CV5). Relevant fractions were combined and volatiles were removed under reduced pressure to afford the desired product as a pale red gum which was used directly in the next step without further purification. 143 mg, 0.392 mmol, 69%)LCMS (2 mm Formic): Rt = 1 .05 mi [MH] = 365. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium t-butanolate; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere; | The 1,10-phenanthroline trifluoroethyl ether copper (I) prepared in Example 1,In a nitrogen atmosphere, a polytetrafluoroethylene magnet was placed in the reactor,A solution of 0.36 mmol of 1,1,10-phenanthroline trifluoroethyl ether copper (I)(Phen) 2Cu (OCH2CF3),0.3 mmol of <strong>[122918-25-6]2-bromo-6-cyanopyridine</strong>,0.3 mmol of sodium tert-butoxide and 3 mL of N, N-dimethylformamide solvent,And heated in a closed system at 80 C for 12 h,Cooled to room temperature, extracted with 3 x 10 mL of ether, the extracts were combined,Concentrated, the residue was silica gel column chromatography,Using ether: n-pentane = 1: 3 as the eluent,To give 2-trifluoroethoxy-6-cyanopyridine at a yield of 84% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 100℃; for 1h;Microwave irradiation; | General procedure: AG10 vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or <strong>[122918-25-6]6-bromopyridinecarbonitrile</strong>(1 eq), boronic acid (2 eq),Na2CO3 (4 eq), and Pd(PPh3)2Cl2(10 mol%). Toluene/EtOH/water/ (2/1/1 mL) were next added. The resulting mixturewas irradiated using the closed vessel mode at 100C for 60 min. The mixture wasthen extracted with dichloromethane, washed with a saturated solution of NaHCO3,dried over MgSO4, and concentrated by rota-evaporation under vacuum.The crude product was purified by flash chromatography, with a pentane /AcOEt (9/1to 7/3) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 100℃; for 1h;Microwave irradiation; | General procedure: AG10 vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or <strong>[122918-25-6]6-bromopyridinecarbonitrile</strong>(1 eq), boronic acid (2 eq),Na2CO3 (4 eq), and Pd(PPh3)2Cl2(10 mol%). Toluene/EtOH/water/ (2/1/1 mL) were next added. The resulting mixturewas irradiated using the closed vessel mode at 100C for 60 min. The mixture wasthen extracted with dichloromethane, washed with a saturated solution of NaHCO3,dried over MgSO4, and concentrated by rota-evaporation under vacuum.The crude product was purified by flash chromatography, with a pentane /AcOEt (9/1to 7/3) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 100℃; for 1h;Microwave irradiation; | General procedure: AG10 vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or <strong>[122918-25-6]6-bromopyridinecarbonitrile</strong>(1 eq), boronic acid (2 eq),Na2CO3 (4 eq), and Pd(PPh3)2Cl2(10 mol%). Toluene/EtOH/water/ (2/1/1 mL) were next added. The resulting mixturewas irradiated using the closed vessel mode at 100C for 60 min. The mixture wasthen extracted with dichloromethane, washed with a saturated solution of NaHCO3,dried over MgSO4, and concentrated by rota-evaporation under vacuum.The crude product was purified by flash chromatography, with a pentane /AcOEt (9/1to 7/3) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 100℃; for 1h;Microwave irradiation; | General procedure: AG10 vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or <strong>[122918-25-6]6-bromopyridinecarbonitrile</strong>(1 eq), boronic acid (2 eq),Na2CO3 (4 eq), and Pd(PPh3)2Cl2(10 mol%). Toluene/EtOH/water/ (2/1/1 mL) were next added. The resulting mixturewas irradiated using the closed vessel mode at 100C for 60 min. The mixture wasthen extracted with dichloromethane, washed with a saturated solution of NaHCO3,dried over MgSO4, and concentrated by rota-evaporation under vacuum.The crude product was purified by flash chromatography, with a pentane /AcOEt (9/1to 7/3) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; toluene; at 100℃; for 1h;Microwave irradiation; | General procedure: AG10 vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or <strong>[122918-25-6]6-bromopyridinecarbonitrile</strong>(1 eq), boronic acid (2 eq),Na2CO3 (4 eq), and Pd(PPh3)2Cl2(10 mol%). Toluene/EtOH/water/ (2/1/1 mL) were next added. The resulting mixturewas irradiated using the closed vessel mode at 100C for 60 min. The mixture wasthen extracted with dichloromethane, washed with a saturated solution of NaHCO3,dried over MgSO4, and concentrated by rota-evaporation under vacuum.The crude product was purified by flash chromatography, with a pentane /AcOEt (9/1to 7/3) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In 1,4-dioxane; at 180℃; for 0.25h;Microwave irradiation; | General procedure: A G10vial in a Microwave 300 vessel was charged with 6-bromopyridinecarboxaldehyde,or <strong>[122918-25-6]6-bromopyridinecarbonitrile</strong> (89 mg, 0.479 mmol, 1 eq), CuI (15 mg, 0.048mmol, 0.1 eq), Pd(PPh3)2Cl2 (28mg, 0.048mmol,0.1 eq), 2-(tributylstannyl) pyridine (278 uL, 0.527 mmol, 1.1 eq)and 6 ml of dioxane. The resulting mixture was irradiated using the closedvessel mode at 180C for 15 min. The reaction mixture was filtered through apad of alumina with diethyl ether. The crude product was purified by flashchromatography on silica gel, with a pentane/AcOEt (95/5) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 85℃; for 2h;Inert atmosphere; | To a solution of Compound 27 (387 mg, 2.40 mmol) and 6-bromopicolinonitrile (Compound 52) (400 mg, 2.19 mmol) in DME (4 mL) and EtOH (4 mL) was added Pd(PPh3)2Cl2 (77 mg, 0.11 mmol) followed by 2M aq. Na2CO3 (2.73 mL, 5.46 mmol). The reaction mixture was purged with nitrogen and stirred at 85 C. for 2 h. After cooling to RT, the reaction was diluted with water and extracted with EtOAc (2*). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, 30-50% EtOAc/hexanes) to give Compound 53 as an off-white solid (404 mg). Yield 84%. LC/MS: m/z=220 [M+H]+ (Calc: 219). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Rhodococcus rhodochrous ATCC BAA 870 cobalt nitrile hydratase; In aq. buffer; at 30℃;pH 7.6;Enzymatic reaction; | General procedure: 1800 muL (90%) Tris buffer (50 mM, pH 7.6) and 200 muL(10%) of methanol or acetone. In a 2 mL Eppendorf, NHase (10 mg) was added followed by Trisbuffer. Nitrile substrate (10 mg dissolved in 200 muL methanol or acetone) was added to the 2 mLEppendorf tube. (If an amine group was present on the nitrile substrate a Tris buffer of pH 9 wasused). The reaction mixture was incubated at 30 C on an ESCO Provocell microplateshaker/incubator (Esco Technologies, Halfway House, South Africa) (199 rpm). The reaction wasallowed to proceed for 24 h, 48 h or 5 d, depending on conversion, as monitored by TLC analysis.Ethyl acetate and water were added to the reaction mixture, and after separation, the organic layerwas concentrated under reduced pressure, and the resulting mixture was then purified by silica gelcolumn chromatography eluting with 20% to 90% ethyl acetate/ hexane. |
Tags: 122918-25-6 synthesis path| 122918-25-6 SDS| 122918-25-6 COA| 122918-25-6 purity| 122918-25-6 application| 122918-25-6 NMR| 122918-25-6 COA| 122918-25-6 structure
[ 450844-27-6 ]
6-Bromo-5-methylpicolinonitrile
Similarity: 0.92
[ 1206248-51-2 ]
6-Bromo-4-chloropicolinonitrile
Similarity: 0.79
[ 113124-06-4 ]
2-Bromo-5,6-dimethylnicotinonitrile
Similarity: 0.75
[ 450844-27-6 ]
6-Bromo-5-methylpicolinonitrile
Similarity: 0.92
[ 1206248-51-2 ]
6-Bromo-4-chloropicolinonitrile
Similarity: 0.79
[ 113124-06-4 ]
2-Bromo-5,6-dimethylnicotinonitrile
Similarity: 0.75
[ 450844-27-6 ]
6-Bromo-5-methylpicolinonitrile
Similarity: 0.92
[ 1206248-51-2 ]
6-Bromo-4-chloropicolinonitrile
Similarity: 0.79
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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