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CAS No. : | 86-58-8 | MDL No. : | MFCD01114698 |
Formula : | C9H8BNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KXJJSKYICDAICD-UHFFFAOYSA-N |
M.W : | 172.98 | Pubchem ID : | 2734380 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 51.57 |
TPSA : | 53.35 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.58 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.09 |
Log Po/w (WLOGP) : | -0.09 |
Log Po/w (MLOGP) : | 0.04 |
Log Po/w (SILICOS-IT) : | -0.17 |
Consensus Log Po/w : | 0.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.1 |
Solubility : | 1.37 mg/ml ; 0.0079 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.8 |
Solubility : | 2.72 mg/ml ; 0.0158 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.59 |
Solubility : | 0.448 mg/ml ; 0.00259 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.88 |
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 |
---|---|---|
74% | A mixture of bromotriazole 93g (50 mg, 0.073 mmol), <strong>[86-58-8]quinolin-8-ylboronic acid</strong> (38.0 mg, 0.219 mmol), potassium phosphate (46.6 mg, 0.219 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (3.00 mg, 6.29 mumol), and Pd2(dba)3 (0.980 mg, 1.070 mumol) was added to a microwave vial and diluted with acetonitrile (183 mul) and butanol (100 muL). The vial was irradiated for 15min @ 140 0C. The reaction mixture was diluted with 200ul of 4N HCl in dioxane and the solvent removed under a stream of nitrogen. The reaction mixture was purified by silica column to afford a white solid after purification (40mg 74%). MS (ESI): m/z = 711.1 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With bis(dibenzylideneacetone)-palladium(0); In toluene; at 110℃; | The 2,6-bis(8?-quinolinyl)pyridine (bqp) ligand was prepared by modification to the route first described by Hammarstroem et al. [8] using Suzuki cross-coupling reaction conditions following the procedures developed by Buchwald and coworkers [19]. For the Suzuki cross-coupling reaction, a catalytic system including palladium(0) bis(dibenzylideneacetone) (Pd(dba)2) and 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (P?) was implemented, which recently has been effective in coupling heterocyclic substrates [20,21]. Reacting <strong>[86-58-8]quinoline-8-boronic acid</strong> and 2,6-dibromopyridine with 1mol% of Pd(dba)2 and 2mol% of P? in toluene at 110C gave bqp in 80% isolated yield (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 2h;Heating / reflux; | The product of part b (250mg), 7-quinoline boronic acid [(114MG),] 2M sodium bicarbonate (0. [7ML),] toluene, ethanol, tetrakis palladium triphenyl phosphine (0) and lithium chloride were heated at reflux for 2 hours. The reaction mixture was concentrated in vacuo, purified using amine resin and then by reverse phase preparative HPLC to give the title compound as a white solid. [IH] NMR (DMSO-d6) 8 8. 81 [(1H,] s), 8.43 [(LH,] d), 8.02-7. 97 [(LH,] m), 7.78-7. 7 [(LH,] m), 7.39 [(LH,] d), 7.04 (2H, m), 4.67 [(2H,] s), 2.2 (3H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene;Heating / reflux; | Description 1; 2-Chloro-4- pyrimidine; Pd (PPh3) 4 (334 mg, 0.29 mmol) was added to a mixture of 2, 4-dichloropyrimidine (861 mg, 5.78 mmol), <strong>[86-58-8]quinoline-8-boronic acid</strong> (1.0 g, 5. 78 mmol), and 2M aqueous sodium carbonate (2.89 ml, 5.78 mmol) in a mixture of toluene (50 ml) and ethanol (10 ml). The mixture was degassed three times and heated at reflux overnight. The reaction mixture was cooled and diluted with EtOAc (50 ml), washed with water (2 x 100 ml), sat NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica: (eluent 2% MeOH in DCM + 0.5% NH40H) to give the title compound as a white solid (650 mg, 46%). 1H NMR (500 MHz, CDCIs) 7.49 (1 H, dd, J8. 3 and 4.2), 7.69 (1 H, t, J7.9 and 7.6), 7.98 (1 H, d, J8.1), 8.25 (1 H, dd, J8. 3 and 1.5), 8.43 (1 H, d, J7.1), 8.46 (1 H, d, J5.2), 8.69 (1 H, d, J5.2), 8.97 (1 H, dd, J3. 9 and 1. 5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane;Heating / reflux; | Description 6; 4-Chloro-6-(quinolin-8-yl)pyrimidine; To a mixture of 4, 6-dichloropyrimidine (1.72 g, 11.6 mmol), <strong>[86-58-8]quinoline-8-boronic acid</strong> (1.0 g, 5. 78 mmol) and tripotassium phosphate (2.46 g, 11.6 mmol) in 1,4- dioxane (50 ml) was added Pd (PPh3) 4 (334 mg, 0.29 mmol). The mixture was degassed three times and heated at reflux overnight. The reaction mixture was cooled and diluted with EtOAc (50 ml), washed with water (2 x 100 ml), sat. NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica: (eluent 2% MeOH in DCM + 0.5% NH40H) to give the title compound as a white solid (200 mg, 14%). 1H NMR (500 MHz, CDCl3) 7.50 (1 H, dd, J8.1 and 4.2), 7.71 (1 H, t, J7.8 and 7. 6), 7.98 (1 H, dd ; J 8.1 and 1.3), 8.26 (1 H, dd, J8.4 and 1.8), 8.41 (1 H, dd, J7.3 and 1.5), 8.56 (1-H, d, J 1. 0), 9.01 (1 H, dd, J4.2 and 2.0), 9.12 (1 H, d, J 1. 0). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.7% | With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 170℃; for 0.666667h;Microwave irradiation; | Example 26; 6-Quinolin-8-yl-N-[4-trifluoromethylphenyl]pyridazin-4-amine; A mixture of Description 8 (100 mg, 0.38 mmol), <strong>[86-58-8]quinoline-8-boronic acid</strong> (126 mg, 0.73 mmol), 2M sodium carbonate (0.365 ml, 0.73 mmol), and Pd (dppf) Cl2 (10 mg," 0. 011 mmol) was heated at 170C for 40 mins in a Smith microwave reactor. The mixture was diluted with dichloromethane (20 ml) and washed with water (2 x 20 ml), sat. NaCl (15 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by PREP-TLC: (eluent 10% MeOH in DCM + 0.5% NH40H), followed by mass-directed HPLC to give the title compound as a white solid (9 ing, 6.7%). lH NMR (500 MHz, DMSO-d6) 7.53 (2 H, d, J8.3), 7.63 (1 H, dd, J8. 4 and 4.2), 7.72 (2 H, d, J8.3), 7.78 (1 H, t, J7. 8 and 7. 4), 7.99 (1 H, d, J2.7), 8.15 (1 H, d, J 8.3), 8.23 (1 H, dd, J7. 1 and 1. 2), 8.51 (1 H, dd, J8. 3 and 1. 7), 9.00 (1 H, d, J2.7), 9.04 (1 H, dd, J4. 2 and 1.7), 9.66 (1 H, s) ; mlz (ES+) 367 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.32% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene;Heating / reflux; | Example 27; 4-Quinolin-8-vl-N- [4-trifluoromethylphenyl]-1*3*5-triazin-2-amine; To a mixture of Description 9 (790 mg, 2.89 mmol), <strong>[86-58-8]quinoline-8-boronic acid</strong> (500 mg, 2.89 mmol) and 2M Sodium carbonate (2.89 ml, 5.78 mmol) in a mixture of toluene (50 ml) and ethanol (10 ml) was added Pd (PPh3) 4 (171 mg, 0.14 mmol), the mixture degassed three times and heated at reflux overnight. The reaction mixture was cooled and diluted with EtOAc (50 ml), washed with water (2 x 100 ml), sat NaCl (100 ml), dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica: (eluent 2% MeOH in DCM + 0.5% NH40H), and product further purified by mass-directed HPLC to give the title compound as a white solid (3.4 mg, 0. 32%). 1H NMR (500 MHz, CDC13) 7.51 (1 H, dd, J8. 4 and 4.2), 7.60 (2 H, d, J8. 3), 7. 68 (2 H, m), 7.86 (2 H, d, J8.3), 8.01 (1 H, dd, J8. 1 and 1.2), 8. 17 (1 H, m), 8.26 (1 H, dd, J8.3 and 1.3), 8.99 (1 H, s), 9.02 (1 H, m) ; mlz (ES+) 368 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 100℃; for 0.166667h;Microwave; | A mixture of 200 mg (0. 97mmol) of 5-bromo-2-thiophenecarboxylic acid, 200mg (1. 16mmol, 1.2 eq. ) of <strong>[86-58-8]8-quinoline boronic acid</strong> and 34mg (0. 05mmol, 5 mol%) of bistriphenylphosphinepalladium (II) chloride in 1. 5mL of 2M Na2CO3 solution and 3 mL of DMF was heated at 100C for 10 min under microwave conditions. The resulting mixture was diluted with 1N HCl, and the precipitate was collected. This solid was dissolved in MeOH and acetone, and this solution was treated with (MgS04) and activated charcoal. The solution was filtered through diatomaceous earth and concentrated. The residual solid was triturated with EtOAc and hexanes to give 220mg (89%) of desired compound as a light orange solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; | The crude tert-butyl 6-triphenylmethyloxy-3(R),5(S)-dihydroxyhexanoate was dissolved in 100 mL of toluene and 6.1 g of <strong>[86-58-8]quinoline-8-boronic acid</strong> was added. Water was removed by azeotropic distillation over a period of 3 hours. The reaction mixture was cooled to room temperature and toluene was removed under reduced pressure. 30 mL of methanol was added and the precipitated solid was filtered to give 11 g of the title product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 20h; | N- (2-t-Butoxycarbonylaminophenyl)-4-bromobenzamide (Method 14; 200 mg, 0.5 mmol), <strong>[86-58-8]8-quinoline boronic acid</strong> (104 mg, 0.6 mmol), tetrakis (triphenylphosphine) palladium (8 mg, 0.007 mmol), 1,2-dimethoxyethane (3 ml) and a saturated aqueous solution of sodium hydrogen carbonate (3 ml) were stirred at 80C under an atmosphere of argon for 20 hours. The mixture was allowed to cool before being partitioned between ethyl acetate and water. The organics were washed with brine, dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by flash column chromatography, eluting with methanol/dichloromethane (0-10%), to give the title compound (201 mg, 84%); NMR Spectrum : (DMSO-d6) : 1.47 (s, 9H), 7.20 (m, 2H), 7.60 (m, 4H), 7.73 (t, 1H), 7.84 (t, 3H), 8.06 (d, 2H), 8.47 (d, 1H), 8.68 (s, 1H), 8.93 (m, 1H), 9.91 (s, 1H), Mass Spectrum: M+H+ : 440. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Step 2 Methyl 2-[3,5-bis(trifluoromethyl)benzoyl]amino}-5-(8-quinolinyl)benzoate Use of methyl 2-[(3,5-bis(trifluoromethyl)benzoyl)amino]-5-iodobenzoate (100 mg, 0.19 mmol) and <strong>[86-58-8]8-quinolineboronic acid</strong> (42 mg, 0.24 mmol) afforded the title compound (50 mg, 51 %) as a white solid by the application of the general procedure J described above. 1H NMR (CDCl3) delta 12.45 (br s, 1H), 9.03-8.95 (m, 2H), 8.55 (s, 2H), 8.49 (d, J=2.2 Hz 1H), 8.23 (dd, J=8.3, 2.0 Hz 1H), 8.09 (s, 1H), 8.02 (dd, J=8.5, 2.2 Hz 1H), 7.84 (dd, J=8.1, 1.5 Hz 1H), 7.78-7.60 (m, 2H), 7.45 (dd, J=8.3, 4.1 Hz 1H), 3.99 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | Step 2 Methyl 2-[(4-methoxybenzoyl)amino]-5-(8-quinolinyl)benzoate Use of methyl 5-iodo-2-[(4-methoxybenzoyl)amino]benzoate (100 mg, 0.24 mmol) and <strong>[86-58-8]8-quinolineboronic acid</strong> (52 mg, 0.30 mmol) afforded the title compound (8 mg, 8%) as a beige solid by the application of the general procedure J described above. 1H NMR (CDCl3) delta 12.05 (br s, 1H), 9.07 (d, J=8.8 Hz 11H), 8.97-8.95 (m, 1H), 8.46 (s, 11H), 8.23 (d, J=8.3 Hz 1H), 8.07 (d, J=8.8 Hz 2H), 7.96 (d, J=8.6 Hz 1H), 7.85 (d, J=8.1 Hz 1H), 7.76 (d, J=7.2 Hz 1H), 7.65-7.59 (m, 1H), 7.46-7.41 (m, 1H), 7.04 (d, J=9.0 Hz 2H), 3.96 (s, 3H), 3.90 (s, 3H); MS m/z (M+1) 413. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 114A 4-formyl-2-(8-quinolinyl)benzonitrile The desired product can be prepared by substituting Example 200A and <strong>[86-58-8]8-quinolinylboronic acid</strong> for 3-bromo-4-fluorobenzaldehyde and 2-methylphenylboronic acid, respectively in Example 1A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; triphenylphosphine;palladium diacetate; In propan-1-ol; water; | EXAMPLE 206C 4-cyano-N-(4-cyanobenzyl)-N-((1-methyl-1H-imidazol-5-yl)methyl)-3-(8-quinolinyl)benzamide A solution of Example 206B (10 mg) and <strong>[86-58-8]8-quinolinylboronic acid</strong> (8.0 mg) in n-propanol (0.8 mL) and water (0.4 mL) was treated with Pd(OAc)2 (1.0 mg), triphenylphosphine (3.0 mg), and 2M Na2CO3 (15 mL), heated to 90 C., and stirred for 2 hours. The mixture was purified by preparative HPLC and lyophilized to provide the desired product. MS (APCI(-)) m/z 517 (M+Cl)-; 1H NMR (300 MHz, DMSO-d6, at 90 C.) delta 8.92 (s, 1H), 8.79 (dd, 1H), 8.45 (dd, 1H), 8.12 (dd, 1H), 7.96 (d, 1H), 7.71-7.39 (m, 1OH), 4.77 (s, 2H), 4.74 (s, 2H), 3.74 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; hydrogenchloride; cesium fluoride;Pd(Ph3P)4; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; | EXAMPLE 247 6-(((4-cyano-3-(8-quinolinyl)phenyl)(1-methyl-1H-imidazol-5-yl)methoxy)methyl)nicotinonitrile trihydrochloride A solution of Example 244A (34 mg, 0.084 mmol) and <strong>[86-58-8]8-quinolinylboronic acid</strong> (23 mg, 0.13 mmol) in 1,2-dimethoxyethane (1.5 mL) was treated with cesium fluoride (32 mg, 0.2 mmol) and Pd(Ph3P)4 (4 mg), purged with argon, heated to 100 C., stirred for 16 hours, and filtered. The filtrate was purified by HPLC on a C18 reverse phase column with acetonitrile/10 mM ammonium acetate, concentrated, lyophilized, dissolved in dichloromethane, treated with 1M HCl in diethyl ether, and concentrated to provide the desired product. MS (ESI(+)) m/z 457 (M+H)+and 489 (M+Na)+; 1H NMR (300 MHz, DMSO-d6) delta 9.09 (s, 1H), 8.97 (dd, 1H), 8.87 (dd, 1H), 8.50 (dd, 1H), 8.31 (dd, 1H), 8.16 (dd, 1H), 8.06 (d, 1H), 7.87 (dd, 1H), 7.79-7.70 (m, 4H), 7.62 (dd, 1H), 7.56 (s, 1H), 6.22 (s, 1H), 4.80 (q, 2H), 3.80 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate;dihydrogen dichloro-bis(di-tert-butylphosphinito-kappaP)palladium(2-); In isopropyl alcohol; at 100℃; for 20h; | Compound IA (4.0 g, 8.8 mmol), <strong>[86-58-8]8-quinolineboronic acid</strong> (3.0 g, 17.6 mmol), POPd (0.088 g, 0.18 mmol), and K2CO3 (3.6 g, 26.4 mmol) in iPrOH (90 mL) were stirred in a preheated 100 0C oil bath under nitrogen for 20 h. The reaction was filtered through celite and concentrated. The material was purified by chromatography on silica gel (gradient 2-5% MeOH in CH2CI2) to give a yellow solid IB (3.27 g , 74%). 1H NMR (500.333 MHz, CDCl3) delta 8.91 (dd, J= 4.0, 1.6 Hz, IH), 8.13 (dd, J= 8.2, 1.5 Hz, IH), 7.74 (dt, J= 9.5, 3.5 Hz, IH), 7.50 (d, J= 2.5 Hz, 2H), 7.37-7.33 (m, 5H), 3.86 (br s, 2H), 3.68 (br s, 2H), 3.59 (br s, 2H), 3.52-3.43 (m, 3H), 3.34-3.23 (m, 2H), 3.03 (s, 3H), 2.57-2.52 (m, 2H), 2.01 (dd, J= 19.3, 7.6 Hz, 2H), 1.44 (s, 9H). MS ES+ 502.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In acetonitrile; at 85℃; for 4h; | Example 19S-fl-fbeta-chlow--fS-quinolinyty-S-ftrifluoromethytyimidazofl^-aJpyridin^-ylJcarbonyl}^- piperidinyl)-l,3-oxazolidin-2-one (Compound 120)[0133] To a mixture of 3-(l-[6-bromo-3-chloro-8-(trifluoromethyl)imidazo[l,2-a]pyridin-2- yl]carbonyl}-4-piperidinyl)-l,3-oxazolidin-2-one (120 mg, 0.24 mmol), <strong>[86-58-8]8-quinolinylboronic acid</strong> (0.36 mmol), and 3M potassium phosphate tribasic (0.72 mL, 2.2 mmol) in acetonitrile (2 niL) was added PdCl2(dppf)-dichloromethane adduct (40 mg, 0.048 mmol). The mixture was heated to 85 0C for 4 hours, cooled to room temperature, quenched with water, and extracted 2 times with dichloromethane. The combined organic layers were concentrated and the residue purified by reverse phase HPLC to give the title compound. LCMS: m/z 544, 546 (M+ 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; toluene; at 100℃; for 18h;Inert atmosphere; | [0182] <Example 12> (Synthesis of compound 6)The synthesized 2,9-dichloro-l,10-phenanthroline was used to synthesize compound 6 according to the following reaction formula. [Chemical Formula 130][0183] Specifically, 100 mg (0.40 mmol) of 2,9-dichloro-l,10-phenanthroline and 278 mg of 8-quinoline-boric acid (1.61 mmol, product of Aldrich Co.) were added to a mixed solvent comprising 3 ml of toluene and 5 ml of DMF, and the mixture was purged with argon gas. Next, 37 mg of Pd (PPh3)4 (0.0321 mmol) and 333 mg of K2CO3 (2.41 mmol) were added and the mixture was stirred at 100C for 18 hours. Column purification was performed to obtain 65 mg of compound 6 at a yield of 37%.Results of mass spectrometry for compound 6MS(FD, 8 kV) Found: m/z 435.4 Qs/f), Calculated: 434.15 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 140℃;Inert atmosphere; Microwave irradiation; | General procedure: To a solution of 13 (30-90 mM) in toluene/EtOH (2:1) in a microwave vial under an argon atmosphere was added Pd(Ph3P)4 (5 mol%) and the mixture stirred for 10 min. An aqueous solution of 1M Na2CO3 (3 eq.) was then added followed by boronic acid (1.1 eq.) or boronic acid pinacol ester (1.1 eq.) and the mixture stirred for 5 min and then heated at 140 C for 21 min unless specified. The resultant mixture was cooled, poured onto ice and extracted with ethyl acetate. The organic extract was then dried (Na2SO4), filtered and solvent removed in vacuo to give the crude product. This was purified or used crude in the following trityl deprotection step as indicated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 150℃; for 0.333333h;Microwave irradiation; | Example 11; 3-(4-quinolin-8-ylphenyl)-1-[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one The mixture of 4-(2-oxo-1-[2-(trimethylsilyl)ethoxy]methyl}-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenyl trifluoromethanesulfonate (500 mg), <strong>[86-58-8]8-quinolineboronic acid</strong> (265 mg), Pd(Ph3P)4 (35.4 mg), 2 M Na2CO3 (1.02 mL) and CH3CN (10 mL) was heated at 150 C. for 20 min under microwave irradiation. The mixture was diluted with sat.NaHCO3aq. at 0 C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give 3-(4-quinolin-8-ylphenyl)-1-[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (410 mg) as white crystals.MS (ESI+): [M+H]+469.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Sub 1-1-1 (1) (3.2g, 20mmol) was dissolved in anhydrous Ether, lowering the temperature of the reaction to -78 , n-BuLi (2.5M inhexane) (1.4g, 22mmol) was slowly added dropwise, and I then, the reaction is stirred for 30 minutes. After lowering the temperature of the reaction back to -78 dropwise Triisopropyl borate (5.64g, 30mmol). Stirring at room temperature, diluted with water and it binds the 2N HCl. After completion of reaction, the organic layer was dried and extracted with water and ethyl acetate and recrystallized with MgSO4 and silicagel column The concentrated organics to give 1.8g Sub 1-1 (1). (Yield: 73%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 95℃; for 24h;Inert atmosphere; | General procedure: A mixture of Pd(PPh3)4 (12 mol%), the corresponding tetrabromide (1 equiv), the quinolinylboronic acid (6 equiv) and K3PO4 (12 equiv, 2M in H2O) was placed in a Schlenk flask under N2. Degassed DMF (20 mL) was added to the mixture and the flask was heated at 95C under N2 for 24 hours. The mixture was then cooled and partitioned by CH2Cl2 and water, and the aqueous layer was washed with CH2Cl2 several times. The organic layers were combined together and dried over Na2SO4. After filtration, the solvent was removed under vacuum, and the residue was separated through a silica-gel column using THF/hexanes as eluent and recrystallized from hexanes/CH2Cl2 or hexanes/CHCl3 to afford the corresponding product as colorless crystalline solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 95℃; for 24h;Inert atmosphere; | General procedure: A mixture of Pd(PPh3)4 (12 mol%), the corresponding tetrabromide (1 equiv), the quinolinylboronic acid (6 equiv) and K3PO4 (12 equiv, 2M in H2O) was placed in a Schlenk flask under N2. Degassed DMF (20 mL) was added to the mixture and the flask was heated at 95C under N2 for 24 hours. The mixture was then cooled and partitioned by CH2Cl2 and water, and the aqueous layer was washed with CH2Cl2 several times. The organic layers were combined together and dried over Na2SO4. After filtration, the solvent was removed under vacuum, and the residue was separated through a silica-gel column using THF/hexanes as eluent and recrystallized from hexanes/CH2Cl2 or hexanes/CHCl3 to afford the corresponding product as colorless crystalline solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 95℃; for 24h;Inert atmosphere; | General procedure: A mixture of Pd(PPh3)4 (12 mol%), the corresponding tetrabromide (1 equiv), the quinolinylboronic acid (6 equiv) and K3PO4 (12 equiv, 2M in H2O) was placed in a Schlenk flask under N2. Degassed DMF (20 mL) was added to the mixture and the flask was heated at 95C under N2 for 24 hours. The mixture was then cooled and partitioned by CH2Cl2 and water, and the aqueous layer was washed with CH2Cl2 several times. The organic layers were combined together and dried over Na2SO4. After filtration, the solvent was removed under vacuum, and the residue was separated through a silica-gel column using THF/hexanes as eluent and recrystallized from hexanes/CH2Cl2 or hexanes/CHCl3 to afford the corresponding product as colorless crystalline solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In 1,4-dioxane; at 100℃;Inert atmosphere; | Methyl 4-chloro-l-[(5-phenyl-l,2,4-oxadiazol-3-yl)methyl]-lH-pyirolo[3,2-c]pyridine-2- carboxylate (30 mg, 0.081 mmole), Pd(OAc)2 (2 mg, 8.91 muiotaetaomicron?), l,l'-bis-(di-t- butylphosphino)ferrocene (4 mg, 8.43 muiotaetaomicron?), K3P04 (52 mg, 0.245 mmole) and quinolin-8- ylboronic acid (19 mg, 0.105 mmole) were combined in a screw cap vial. To this was added 1,4- dioxane (0.5 mL). N2 was bubbled through the mixture for 10 seconds. The vial was capped then heated to 100 C. After stirring overnight the mixture was cooled to RT. 2M NaOH (0.122 mL, 0.244 mmole) was added and the mixture heated to 60 C. After 2 hr 250 mu?. 2M NaOH was added and heating continued. After 3 hr the mixture was cooled to RT, filtered using a 0.45 mupiiota PTFE syringe filter, then concentrated. The crude material was taken up in DMSO and acidified with TFA. The resulting solution was purified by preparative reversed-phase HPLC (2 lxl 00mm Phenomenex AXIA-Gemini-NX, CH3CN/water containing 0.1% TFA over 18 min at 20 mL/min) to the TFA salt of the title compound (13 mg, 29%) as a tan solid. ? NMR (499 MHz, DMSO): delta 8.96 (dd, J = 4.2, 1.7 Hz, 1 H); 8.81 (d, J = 6.8 Hz, 1 H); 8.66 (dd, J = 8.3, 1.7 Hz, 1 H); 8.50 (d, J = 6.9 Hz, 1 H); 8.41 (d, J = 8.2 Hz, 1 H); 8.31 (d, J = 7.1 Hz, 1 H); 8.08 (d, J = 7.7 Hz, 2 H); 7.96-7.91 (m, 1 H); 7.77-7.70 (m, 2 H); 7.67-7.61 (m, 2 H); 7.42 (s, 1 H); 6.36 (s, 2 H). HRMS (ESI) calc (M+H)+ = 448.1404, found 448.1404. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; sodium carbonate; triphenylphosphine; In water; isopropyl alcohol; at 85℃; for 0.75h; | General procedure: Mixtures of N-(4-amino-2-methylquinolin-6-yl)-4-iodobenzamide (17qq) (100mg, 0.17mmol), the corresponding quinolinyl boronic acid (0.17mmol, 1.1equiv), Pd(OAc)2 (1.1mg, 0.005mmol), PPh3 (3.9mg, 0.015mmol) and Na2CO3 (21.0mg, 0.198mmol) in 2:1 i-PrOH/H2O (10mL) were heated to 85C in a sealed tube under an argon atmosphere. After 45min the mixtures were cooled to room temperature and filtered through a plug of celite. The filtrates were dissolved in EtOAc (150mL), washed with brine (3×30mL), dried (MgSO4), and concentrated to yield crude product that was co-evaporated with diethyl ether. The solids thus obtained were dissolved in 1:1 TFA/DCM (20mL) and stirred at room temperature for 4h. The solutions were evaporated in vacuo to give crude products which were purified by recrystallization from MeOH/CHCl3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; sodium carbonate; triphenylphosphine; In water; isopropyl alcohol; at 85℃; for 0.75h; | General procedure: Mixtures of N-(4-amino-2-methylquinolin-6-yl)-4-iodobenzamide (17rr; 100mg, 0.17mmol), the corresponding quinolinyl boronic acid (0.17mmol, 1.1equiv), Pd(OAc)2 (1.0mg, 0.005mmol), PPh3 (3.9mg, 0.015mmol) and Na2CO3 (21.0mg, 0.198mmol) in 2:1 i-PrOH/H2O (10mL) were heated to 85C in a sealed tube under an argon atmosphere. After 45min the mixtures were cooled to room temperature and filtered through a plug of celite. The filtrates were dissolved in EtOAc (150mL), washed with brine (3×30mL), dried (MgSO4), and concentrated to yield crude product that was co-evaporated with diethyl ether. The solids thus obtained were dissolved in 1:1 TFA/DCM (20mL) and stirred at room temperature for 4h. The solutions were evaporated in vacuo to give crude products which were purified by recrystallization from MeOH/CHCl3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With palladium diacetate; sodium carbonate; triphenylphosphine-3,3?,3?-trisulfonic acid trisodium salt; In water; acetonitrile; at 100℃; for 4h;Inert atmosphere; | General procedure: Method E. To a stirred solution of 6-chloropurine riboside (2) (1equiv) in H2O/CH3CN (2:1, 6mL/mmol), Pd(OAc)2 (0.05equiv), TPPTS (0.15equiv), arylboronic acid (1.25equiv) and sodium carbonate (3equiv) were added under argon atmosphere. The reaction mixture was warmed to 100C (or 80C when mentioned) and monitored by LC-MS and TLC. When the reaction was complete, the mixture was cooled to room temperature, neutralized by addition of 1M aqueous HCl, and concentrated under reduce pressure. The residue was purified by silica gel chromatography or by preparative HPLC on a C18 reverse-phase column to yield the title compound 5. |
Tags: 86-58-8 synthesis path| 86-58-8 SDS| 86-58-8 COA| 86-58-8 purity| 86-58-8 application| 86-58-8 NMR| 86-58-8 COA| 86-58-8 structure
[ 406463-06-7 ]
6-Quinolineboronic acid pinacol ester
Similarity: 0.73
[ 852362-25-5 ]
Quinoxalin-6-ylboronic acid hydrochloride
Similarity: 0.72
[ 406463-06-7 ]
6-Quinolineboronic acid pinacol ester
Similarity: 0.73
[ 1021868-08-5 ]
5-Quinolineboronic Acid Pinacol Ester
Similarity: 0.72
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