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CAS No. : | 635305-47-4 | MDL No. : | MFCD05663877 |
Formula : | C12H16BClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CHQKHVZXPNHWEA-UHFFFAOYSA-N |
M.W : | 238.52 | Pubchem ID : | 10037225 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 67.93 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.24 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.54 |
Log Po/w (WLOGP) : | 2.64 |
Log Po/w (MLOGP) : | 2.28 |
Log Po/w (SILICOS-IT) : | 2.47 |
Consensus Log Po/w : | 2.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.76 |
Solubility : | 0.0414 mg/ml ; 0.000174 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.61 |
Solubility : | 0.0582 mg/ml ; 0.000244 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.62 |
Solubility : | 0.00573 mg/ml ; 0.000024 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
75% | In toluene; at 20℃; for 2h; | The title compound (75%, oil) was prepared from 3-chlorophenylboronic acid and pinacol. 1H NMR (300 MHz, CDCl3): delta 1.36 (s, 12H), 7.30 (t, 1H), 7.42 (dt, 1H), 7.68 (d, 1H), 7.78 (bd, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 0.5h;Heating / reflux; | Example 41 3-(3-Chloro-phenyl)-5-[3-methyl-4-(4-[1,2,3]triazol-1-yl-butyl)-phenoxymethyl]-pyridine Preparation of 3-Chloromethyl-5-(3-chloro-phenyl)-pyridine i) 5-(3-Chloro-phenyl)-nicotinic acid methyl ester 104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of <strong>[635305-47-4]3-chlorophenylboronic acid pinacol ester</strong> 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.14 g (72%) of 5-(3-Chloro-phenyl)-nicotinic acid methyl ester MS: 248.2 (ESI+) 1H-NMR(400 Hz, [D6]DMSO): delta=3.95(s, 3H, O-CH3), 7.54(m, 2H, Ar-Cl), 7.79(d, 1H, Ar-Cl), 7.92(s, 1H, Ar-Cl), 8.51(s, 1H, pyridine), 9.10(s, 1H, pyridine), 9.17(s, 1H, pyridine) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 0.5h;Heating / reflux; | Example 40 2-(3-Chloro-phenyl)-6-[3-methyl-4-(4-[1,2,3]triazol-1-yl-butyl)-phenoxymethyl]-pyridine Preparation of 2-Chloromethyl-6-(3-chloro-phenyl)-pyridine i) 6-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester 104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of <strong>[635305-47-4]3-chlorophenylboronic acid pinacol ester</strong> 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.42 g (83%) of 6-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester MS: 248.1 (ESI+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv) followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg of NaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0-5 C followed by B2pin2 (2, 381 mg, 1.5 mmol, 3.0equiv) in MeOH (1.0 mL). This mixture was stirred 60 min.H2O (10 mL) was added to the reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layers were washed with sat. NaHCO3, dried over Na2SO4, followed by evaporation, and the crude residue was purified by flash chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In diethyl ether; at 20℃; for 4h; | General procedure: To a solution of aniline (1 mmol) in 3 ml of distillated acetonitrile, at 0C, is added boron trifluoride etherate (1.5mmol 0.4 ml) and the solution is stirred for 5 minutes. Isoamyl nitrite (1.2 mmol, 0.2 ml) is then slowly added and thesolution is stirred for 15 minutes. Diisopropylamino borane (4 mmol, 0.6 ml) is then slowly added and the mixture isallowed to be stirred at room temperature for 3 hours. The reaction is then quenched, at 0C, by the slow addition of 2ml of distillated methanol and stirred 1 hour at room temperature. The mixture is concentrated under vacuum and asolution of pinacol (1.3 mmol, 153 mg) in 2 ml of diethyl ether is added and the mixture is stirred 4 hours at roomtemperature. 10 ml of diethyl ether is then added and the crude is washed three time with 6 ml of a aqueous solution of copper chloride (50 g/L). The organic phase is then filtered and died over Na2SO4 and concentrated under vacuum toafford pure aryl boronate. 113 mg of 2-(4-methoxy-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were obtained following the generalprocedure B using 123 mg of 4-methoxyaniline as a pale yellow oil, yield: 52.5%. 1H NMR (300 MHz, CDCl3) delta 7.75 (d, J= 8.7 Hz, 2H) 6.90 (d, J= 8.7 Hz, 2H) 3.83 (s, 3H) 1.33 (s, 12H). 11B NMR (100 MHz, CDCl3) delta 31.0513C NMR (75 MHz, CDCl3) deltaMS (EI) tR= 9.05 min; m/z: 234 (M+., 100%). 143 mg of 2-(3-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were obtained following the general procedureD according to example 3, using 226 mg of 3-chlorobenzenediazonium tetrafluoroborate as a pale yellow oil,with an isolated yield of 70%.1H NMR (300 MHz, CDCl3) delta 7.78 (s, 1H) 7.67 (d, J = 7.3 Hz, 1H) 7.42 (d, J = 8.1 Hz, 1H) 7.30 (t, J = 7.7 Hz, 1H)11B NMR (100 MHz, CDCl3) delta 30.4013C NMR (75 MHz, CDCl3) delta 134.7; 134.18; 132.79; 131.40; 129.32; 84.29; 25MS (EI) tR = 8.43 min; m/z: 238.5 (M+., 100%) |
68% | With p-phenylpyridine; potassium methanolate; In tert-butyl methyl ether; at 85℃; for 12h; | General procedure: According to the method described in Scheme 1) above,It is possible to synthesize aryl borates with different aromatic ring substituents (as shown in Table 1).The resulting aryl borates are known compounds, and their characterization data are consistent with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(2R,4R)-5-(4-Bromo-phenyl)-2-hydroxy-4-[(1-hydroxy-1H-1,2,3-triazole-4-carbonyl)-amino]-pentanoic acid ethyl ester (120 mg, 281 mumol) and <strong>[635305-47-4]3-chlorophenylboronic acid, pinacol ester</strong> (120 mg, 506 mumol) were combined with K2CO3 (116 mg, 842 mumol), EtOH (3 mL), and water (0.8 mL). SilicaCatDPP-Pd (280 mumol/g loading; 1 mg, 28 mumol) was then added and the mixture was heated at 90 C. and the reaction monitored by LC/MS. The reaction was stopped after 2 hours, and the mixture was filtered, concentrated and purified (C18 reverse phase column; 30-70% MeCN in water with 0.05% TFA). EtOH (5.0 mL, 86 mmol) and 4 M HCl in dioxane (1.5 mL, 6.0 mmol) was added and the resulting mixture was stirred at room temperature for 40 minutes, then concentrated and purified (C18 reverse phase column; 30-90% MeCN in water with 0.05% TFA) to yield the title compound (20 mg; purity 95%). MS m/z [M+H]+ calc'd for C22H23ClN4O5, 459.14. found 459.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1-Hydroxy-1H-1,2,3-triazole-4-carboxylic acid (17.6 mg, 136 mumol) and HCTU (56.4 mg, 136 mumol) were combined in DMF and stirred for 5 minutes at room temperature. DIPEA (71.2 mul, 409 mumol) and (2R,4R)-4-amino-5-(4-bromophenyl)-2-hydroxypentanoic acid ethyl ester (43 mg, 140 mumol) were added and the resulting mixture was stirred for 10 minutes. The reaction mixture was evaporated under reduced pressure and purified (C18 reverse phase column). The purified material was combined with <strong>[635305-47-4]3-chlorophenylboronic acid, pinacol ester</strong> (48.1 mg, 202 mumol), K2CO3 (41.8 mg, 302 mumol), EtOH (1 ml) and water (0.3 ml). Oxygen was removed (high vacuum) and SilicaCatPd(0) (0.09 mmol/g loading; 112 mg, 10.1 mumol) was quickly added under nitrogen. The mixture was microwaved at 100 C. for 20 minutes, then concentrated. The material was redissolved in AcOH and purified by preparative HPLC to yield the title compound (12 mg; purity 95%). MS m/z [M+H]+ calc'd for C20H19ClN4O5, 431.10. found 431.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃;Inert atmosphere; Sealed tube; | EXAMPLE 66 : 5 -(3 -chlorophenyl)- 1 -( 4-methoxybenzyl)-3 -methyl- 1 H-pyrazolo Gamma3 A- blpyridine To a stirred solution of 5-bromo-l-(4-methoxybenzyl)-3-methyl-lH-pyrazolo[3,4-b]pyridine (7) (100 mg, 0.301 mmol, 1 eq) and 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (95) (71 mg, 0.301 mmol, 1 eq) in 1 ,2-dimethoxyethane (10 mL) was added Cs2C03 (244 mg, 0.752 mmol, 25 eq) 2M aqueous solution followed by degassing, purging with N2 for 15 min and addition of Pd(PPh3)4 (13 mg, 0.012 mmol, 0.04 eq). The reaction mixture was heated at 100C in a sealed tube overnight. After completion of the reaction the mixture was partitioned between ethyl acetate and water and the organic layer was separated and again extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and the solvent completely distilled off to get the crude. The crude was passed through 100-200 mesh silica gel eluting the pure compound at 50% ethyl acetate in hexane as off-white coloured solid compound 96 (60 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9 mg | A. (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-(oxalylamino)pentanoic Acid A solution of ethyl oxalyl chloride (70.7 muL, 0.6 mmol) in DIPEA (165 muL, 0.9 mmol) was added to a solution of (2R,4R)-4-amino-5-(4-bromophenyl)-2-hydroxypentanoic acid ethyl ester (100 mg, 0.3 mmol) and DCM (0.7 mL), and the resulting mixture was stirred at room temperature for 10 minutes, followed by evaporation of the solvent under reduced pressure. 3-Chlorophenylboronic acid, pinacol ester (112 mg, 468 mumol), K2CO3 (97 mg, 702 mumol), EtOH (2 mL), and water (0.6 mL) were added, followed by the addition of SilicaCatPd(0) (0.09 mmol/g loading, 260 mg, 23.4 mumol). The mixture was heated at 120 C. for 20 minutes. The reaction mixture was concentrated and 10 M of aqueous NaOH (316 muL) and THF (4.0 mL) with 1 drop of MeOH was added. The resulting mixture was stirred at room temperature for 1 hour. The residue was dissolved in AcOH and purified by preparative HPLC to yield the title compound (9 mg, purity 95%). MS m/z [M+H]+ calc'd for C19H18ClNO6, 392.08; found 392.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Example 3: General procedure D for the synthesis of the arylpinacolboronates by arylation of diisopropylaminoborane, catalysed by ferrocene (1%), followed by methanolysis and transesterification In a dried tube reactor under argon as described in example 2, the arenediazonium salt (1 mmol) and the ferrocene (IotaOmicronmuiotaetaomicronIota, 1.8mg) were dissolved in 2mL of anhydrous CH3CN. Diisopropylaminoborane (2mmol, 226mg) was then added to the solution and the mixture was stirred for 2h30 at room temperature. The reaction mixture was quenched by a slow addition of anhydrous MeOH at 0C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol was added in Et20 (2mL), the mixture was stirred 4h at room temperature. The crude mixture was washed with a 50g/L CuCl2 solution (2 x 5mL). The organic layer were separated, dried over Na2S04, filtered and concentrated to dryness. The resulted oil was dissolved with CH2C12 and filtered of a pad of silica gel, eluting with CH2C12 to afford the corresponding boronate. Example 33: Synthesis of the arylpinacolboronates by arylation of diisopropylaminoborane., catalysed by a titanocene (1%), followed by methanolysis and transesterification Compounds VIAI to VIA22, IA24 and VIA26 were prepared using the procedure D (example 3), by replacing the ferrocene (1%) by the titanocene Cp2TiCl2 (1%). The yields are shown in the table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; at 20℃; for 4h;Inert atmosphere; | General procedure: In a dried tube reactor under argon, were dissolved the diazonium salt (1 mmol) and titanocenedichloride (10mumol, 2.5mg) in 2mL of anhydrous CH3CN. Diisopropylaminoborane (2mmol 226mg) is then added to the solution and stirred for 2h30 at room temperature. The reaction mixture is quenched by a slow addition of anhydrous MeOH at 0C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol is added in Et2O (2mL), the mixture is stirred 4h at room temperature. The crude mixture is washed with a 50g/L CuCl2 solution (2 x 5mL). The organic layer is separated, dried over Na2SO4, filtred and concentrated to dryness. The resulted oil is dissolved with CH2Cl2 and filtered of a pad of silica gel, eluting with CH2Cl2 to afford the corresponding boronate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With magnesium; In tetrahydrofuran; at 25℃; for 3h;Inert atmosphere; | General procedure: To a solution containing 4-IboxBpin (0.651 g,2.0 mmol) and anhydrous THF (8 mL) under Ar, Mg turnings (0.048 g,2.0 mmol) were added. The corresponding halide reagent (2.0 mmol) wasthen introduced dropwise over 5 min with constant stirring at 25 C. Thereaction was complete after 3 h, as evidenced by the disappearance of4-IboxBpin (d +21.6) via 11B NMR. 1 M HCl (3 mL) was then added to thereaction flask and left to stir for 5 min. The reaction mixture was thentransferred to a separatory funnel and extracted with diethyl ether(3 15 mL). The combined organic layers were dried over anhydrous MgSO4,filtered, and dried in vacuo, (25 C, 1 Torr) to afford the correspondingpinacolboronate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere; | 3-Bromo-1-methyl-6-nitroquinoline -4 (1H) - one 3c (237mg, 0.839mmol), 3- chlorophenyl boronic acid pinacol ester (200mg, 0.837mmol, using a known method "OrganicLetters, 2011,13 (13), 3312-3315" prepared derived), [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride (31mg, 0.042mmol), sodium carbonate ( 178mg, 1.68mmol) was suspended in 12mL of N, N- dimethylformamide and water (V / V = 5: 1) mixed solvent, and purged with argon three times, 100 refluxed for 16 hours.The reaction solution was concentrated under reduced pressure, the resulting thin layer chromatography with a developing solvent system A and the residue was purified to give the title product 3- (3-chlorophenyl) -1-methyl-6-nitroquinoline -4 (1H) - one 8a (270mg, yellow solid), yield: 100%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 24h;Inert atmosphere; | General procedure: To a solution under N2 of3-bromo-6-chloro-imidazo[1,2-b]pyridazine (1 g, 4.3 mmol) in dioxane (45 mL), Pd[P(C6H5)3]4(0.248 g, 0.2 mmol), 5-indole-5-boronic acid (0.728 g, 4.51 mmol) and Na2CO3(2 M, 7.7 mL) were added. The mixture was stirred for 21 h at 100 C. Thereaction was monitored by TLC. The solvent was evaporated under reducedpressure. The crude residue was diluted and stirred in AcOEt and ammoniumchloride solution (saturated). The product was extracted with AcOEt, and theorganic layer was washed with NaCl solution. The organic layer was dried overNa2SO4, filtered, and evaporated under reduced pressure.The crude residue was purified by chromatography on silica gel using DCM-AcOEt(6:4) afforded 6a in 72% yield(0.840 g) as a light green powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 21h;Inert atmosphere; | General procedure: To a solution under N2 of3-bromo-6-chloro-imidazo[1,2-b]pyridazine (1 g, 4.3 mmol) in dioxane (45 mL), Pd[P(C6H5)3]4(0.248 g, 0.2 mmol), 5-indole-5-boronic acid (0.728 g, 4.51 mmol) and Na2CO3(2 M, 7.7 mL) were added. The mixture was stirred for 21 h at 100 C. Thereaction was monitored by TLC. The solvent was evaporated under reducedpressure. The crude residue was diluted and stirred in AcOEt and ammoniumchloride solution (saturated). The product was extracted with AcOEt, and theorganic layer was washed with NaCl solution. The organic layer was dried overNa2SO4, filtered, and evaporated under reduced pressure.The crude residue was purified by chromatography on silica gel using DCM-AcOEt(6:4) afforded 6a in 72% yield(0.840 g) as a light green powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With pyridine; cesium fluoride; In dimethyl sulfoxide; at 105℃; for 2h;Inert atmosphere; Schlenk technique; | General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv) and bispinacolatodiboron (254 mg, 1 mmol, 2 equiv). Under an argon atmosphere, freshly distilled DMSO (0.4 mL), the appropriate aryl iodide (0.5mmol), and pyridine (0.4 to 1 equiv) were added successively. The reaction mixture was heated to 105 C and stirred for 2 h under argon. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With sodium t-butanolate; In tetrahydrofuran; toluene; at 50℃; for 6h;Sealed tube; | General procedure: 1-Chloro-4-iodobenzene (48 mg, 0.20 mmol), 48 mg, 0.20 mmol)1,1-Dibornathethane (2, 107 mg, 0.30 mmol) and sodium tert-butoxide base (38 mg, 0.40 mmol) were placed in a 4 mL vial. Toluene / tetrahydrofuran (2.0 mL, 1: 1 mixed solution) was then added.The vial was reacted for six hours at 80 C sealed with a PTFE / silicone coated cap.The reaction solution was filtered through celite with dichloromethane, and the organic material was concentrated under reduced pressure. The products were then separated and purified on silica gel column chromatography Phi 2.0 cm × 8 cm under the specified eluent conditions under n-hexane: diethyl ether, 10: 1 eluent. As a result 2- (4-Chlorophenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane boronated compound was produced. (32 mg, 67% yield); The procedure of Example 3 was followed except that aryl iodide was changed according to the following reaction formula (3), and the results are shown in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In water; isopropyl alcohol; at 100℃; | Pd(PPh3)4 (23 mg, 0.02 mmol), NaHCO3 (42 mg, 0.495 mmol), (2-chlorophenyl)(2-chloropyridin-3-yl)methanone (50 mg, 0.198 mmol) and <strong>[635305-47-4]2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (57 mg, 0.238 mmol) were dissolved in 1 mL of iPrOH/H2O : 4/1 . The reaction mixture was purged three times with Ar and stirred overnight at 100C. The reaction mixture was concentrated to dryness and directly purified by semi-preparative HPLC (0-100% of CH3CN in H2O) which provided after lyophilization 17 mg (26%) of the title compound 8 as a colorless solid. 1H NMR (400 MHz, CDCl3) delta=8.93 - 8.83 (m, 1H), 8.12 (dt, J= 6.8 Hz, 3.4 Hz, 1H), 7.59 - 7.50 (m, 1H), 7.45 - 7.38 (m, 1H), 7.34 - 7.10 (m, 7H); MS (ESI+) m/z: 329.2 [M+H+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With dipotassium peroxodisulfate; silver(I) acetate; palladium diacetate; trifluoroacetic acid; In dichloromethane; at 25℃; for 6h; | The volume ratio of trifluoroacetic acid to dichloromethane at 25 C is 3:1 (1.5 ml : 0.5 ml)2-methyl-indole, hydrazine-dimethylcarbamoyl phenolate (0.2 mmol, added to the solvent)0.0358 g) and trichlorophenylboronic acid pinacol ester (0.0952 g), while adding 0.1620 g of oxidizing agent potassium persulfate, 0.0017 g of silver acetate, 0.0048 g of palladium acetate, and reacting for 6 h.After the end of the reaction, anhydrous potassium carbonate was added, washed with distilled water and extracted with ethyl acetate.The organic layer was obtained and dried, and the obtained product was separated by column chromatography.Wherein the ratio of the developing agent is ethyl acetate: petroleum ether = 1:7, and the separated product is subjected to distillation under reduced pressure.Drying under vacuum at 60 C gave the product 0.0452 g.The yield was 78%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium carbonate; In Dimethyl ether; water; at 100℃; for 8h;Inert atmosphere; | General procedure: To a suspension of 4a (0.1 g, 0.21 mmol) and (1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid (0.057 g,0.25 mmol) in dimethyl ether (DME)/H2O (4 mL) were added Na2CO3(0.06 g, 0.63 mmol) and Pd(dppf)2Cl2 (0.034g, 0.04 mmol) under argon atmosphere, which was allowed to react at 100 C for 8 h. After cooling, water (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (15 mL×3). The organic layer was driedover MgSO4. The solvent was removed in vacuo and the residue waspurified by silica gel chromatography (Developing solvent: PE/EA=3/1) to give 5a (0.09 g, yield 75.2%). |
Tags: 635305-47-4 synthesis path| 635305-47-4 SDS| 635305-47-4 COA| 635305-47-4 purity| 635305-47-4 application| 635305-47-4 NMR| 635305-47-4 COA| 635305-47-4 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
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 |
Sorry,this product has been discontinued.
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