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CAS No. : | 849061-98-9 | MDL No. : | MFCD07369725 |
Formula : | C7H6BFO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YJXJCPZHXDDRNH-UHFFFAOYSA-N |
M.W : | 167.93 | Pubchem ID : | 16217829 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 41.61 |
TPSA : | 57.53 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.05 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.39 |
Log Po/w (WLOGP) : | -0.26 |
Log Po/w (MLOGP) : | 0.08 |
Log Po/w (SILICOS-IT) : | -0.16 |
Consensus Log Po/w : | 0.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.36 |
Solubility : | 7.25 mg/ml ; 0.0432 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.16 |
Solubility : | 11.5 mg/ml ; 0.0685 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.51 |
Solubility : | 5.2 mg/ml ; 0.031 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
52% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 105℃; for 18.0h; | Reference Example 107 tert-butyl [4-(2-fluoro-3-formylphenyl)-5-(phenylsulfonyl)thiophen-2-yl]methyl}methylcarbamate tert-Butyl [4-bromo-5-(phenylsulfonyl)-2-thienyl]methyl}methylcarbamate (257 mg), <strong>[849061-98-9](2-fluoro-3-formylphenyl)boronic acid</strong> (116 mg), sodium carbonate (152 mg) and tetrakis(triphenylphosphine) palladium(0) (66 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the suspension was stirred under a nitrogen atmosphere at 105 C. for 18 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1?4:1) to give the title compound as a colorless amorphous solid (147 mg, yield 52%). 1H-NMR (CDCl3) delta: 1.50 (9H, s), 2.93 (3H, s), 4.56 (2H, br), 6.86 (1H, s), 7.29-7.35 (3H, m), 7.47-7.52 (3H, m), 7.58-7.62 (1H, m), 7.88-7.93 (1H, m), 10.19 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; acetonitrile; at 70℃; for 21.0h;Inert atmosphere; | 1.2 3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorobenzaldehyde 500 mg of 6-bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 473 mg of <strong>[849061-98-9]2-fluoro-3-formylbenzeneboronic acid</strong> and 93 mg of tetrakis(triphenylphosphine)palladium are placed under a stream of argon in a round-bottomed flask comprising a mixture, degassed beforehand under a stream of argon, of 5 ml of acetonitrile, 5 ml of toluene and 6 ml of a 2M sodium carbonate solution. The reaction mixture is heated at 70 C. for 21 h. After cooling, the reaction mixture is diluted with ethyl acetate and water and then the organic phase is separated, dried and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/ethyl acetate 98/02 mixture. 324 mg of compound are obtained. 1H NMR spectrum (d6-DMSO, delta in ppm): from 7.45 to 7.55 (m, 4H); 7.7 (d, 1H); 7.9 (m, 1H); from 7.95 to 8.05 (m, 3H); 8.5 (s, 1H); 8.9 (s, 1H); 10.35 (s, 1H). M+H=351. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; In 1,4-dioxane; water; at 90℃; for 2.0h;Inert atmosphere; Microwave irradiation; | To a solution of 8-bromo-N-tert-butyl-1- (3, 5-dichlorophenyl) -7-methoxy-N-methyl-1, 4-dihydrochromeno [4, 3-c] pyrazole-3-carboxamide (50 mg, 0.093 mmol) in dioxane/H2O (5/1, 2 mL) were added <strong>[849061-98-9]2-fluoro-3-formylphenylboronic acid</strong> (35 mg, 0.186 mmol) , KF (11 mg, 0.186 mmol) , and Pd (dppf) Cl2 (14 mg, 0.019 mmol) at RT under nitrogen. The reaction mixture was stirred at 90 for 2h under MW conditions. The reaction mixture was directly purified by Combi-Flash (mobile phase: acetonitrile/water (10 mM NH4HCO3) to afford N-tert-butyl-1- (3, 5-dichlorophenyl) -8- (2-fluoro-3-formylphenyl) -7-methoxy-N-methyl-1, 4-dihydrochromeno [4, 3-c] pyrazole-3-carboxamide (20 mg, 37 ) as a white solid. LCMS m/z [M+H] + 582. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In methanol; toluene; at 80℃; for 2.5h;Inert atmosphere; Microwave irradiation; | General procedure: A vial equipped with magnetic spin vane was charged with [[3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate (0.203 g; 0.60 mmol; Ex IV-24), 4-formylphenyl boronic acid (0.099 g; 0.66 mmol), and PdCl2(dppf).CH2Cl2(0.012 g; 0.015 mmol), was sealed with a septum and evacuated/backfilled with N2(×3). PhMe/EtOH (4:1, 3 mL) and 2M Na2CO3(0.72 mL; 1.44 mmol) were added through the septum via syringe and the mixture was stirred at 80 C. for 2.5 h. Upon cooling, the mixture was partitioned between EtOAc/water and the layers were separated. The aqueous layer was extracted with EtOAc (×2), combined organics were washed (water, brine), dried over Na2SO4and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum/film.Used IV-32 and 2- fluoro-3-formyl phenyl boronic acid. Note 3 Also prepared by microwave heating. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.8% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃;Inert atmosphere; | Under argon atmosphere to a mixture of THF (25 mL) and water (10 mL) were addedpotassium carbonate (2.76 g, 20 mmol), <strong>[849061-98-9]2-fluoro-3-formylphenylboronic acid</strong> (1.00 g, 5.95mmol), 3,4-dichlorobromobenzene (1.22 g, 5.41 mmol), and Pd(PPh3)4 (188 mg, 0.16 mmol). The reaction was heated to 80 C overnight and the morning after quenched with aqueous HC1 (1 M), and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried using MgSO4, and solvent was removed in vacuo giving the crude product. Thecmde was purified with a gradient column chromatography from EtOAc/Hexane 1:9 affording awhite solid in 55% yield (0.80 g). ?H NMR (400 MI-Tz, DMSO-d6) oe ppm 7.49 (dd, J=10.39,8.68 Hz, 1 H) 7.62 - 7.74 (m, 2 H) 7.96 (dd, J=1.71, 0.73 Hz, 1 H) 8.02 - 8.15 (m, 2 H) 10.23 (s,1 H). ?3C NMR (101 MHz, DMSO-d6) oe ppm 117.92, 118.12, 124.49, 124.58, 127.40, 128.61,129.04, 131.27, 131.52, 132.33, 134.86, 134.89, 135.32, 135.41, 138.97, 162.13, 164.71, 188.30,188.34. HRMS (m/z): [M + Hj, calcd for C13H7C12FO, 268.9931; found, 268.9936. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In water; toluene; at 100℃;Inert atmosphere; | General procedure: To a suspension of 17 (500 mg, 2.05 mmol) and (2,6-difluoro-3-formylphenyl)boronic acid (495 mg, 2.66 mmol) in toluene(10 mL)/H2O (1.0 mL) were added K3PO4 (1.30 g, 6.15 mmol), Pd(OAc)2 (46.0 mg, 0.20 mmol), and SPhos (84.1 mg, 0.20 mmol)under an argon atmosphere. After being stirred at 100 C overnight,(2,6-difluoro-3-formylphenyl)boronic acid (495 mg, 2.66 mmol),Pd(OAc)2 (92.0 mg, 0.41 mmol), and SPhos (168 mg, 0.41 mmol)were added to the mixture. After being stirred at 100 C for 3 h,(2,6-difluoro-3-formylphenyl)boronic acid (495 mg, 2.66 mmol),Pd(OAc)2 (92.0 mg, 0.41 mmol), SPhos (168 mg, 0.41 mmol), andK3PO4 (1.30 g, 6.15 mmol) were added to the mixture. The mixturewas stirred at 100 C overnight. After being cooled to room temperature,the mixture was diluted with H2O and CHCl3. The mixturewas filtered, and the filtrate was separated. The organic layerwas washed with H2O and brine, dried over Na2SO4, and concentratedin vacuo. The residue was purified by column chromatographyon silica gel (hexane/CHCl3/EtOAc = 1:9:0 to 2:18:5) to givethe product (149 mg, 24%) as a pale yellow solid. 1H NMR(DMSO-d6): d 3.65-3.72 (4H, m), 3.75-3.82 (4H, m), 7.44 (1H, dd,J = 9.0, 9.0 Hz), 7.93 (1H, ddd, J = 8.3, 8.3, 6.6 Hz), 8.54-8.58 (2H,m), 10.21 (1H, s); MS (ESI) m/z [M+H]+ 306. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 80℃; for 2.5h;Inert atmosphere; | General procedure: To a solution of 4-(5-bromopyrimidin-2-yl)morpholine (17;4.10 g, 16.8 mmol) and ethyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (6.34 g, 21.8 mmol) in DME(82 mL)/H2O (41 mL) were added Na2CO3 (5.34 g, 50.4 mmol),and Pd(PPh3)4 (1.94 g, 1.68 mmol) under an argon atmosphere.The mixture was stirred at 80 C for 2.5 h. After being cooled toroom temperature, the mixture was diluted with H2O and EtOAc.The mixture was filtered, and the filtrate was separated. Theorganic layer was washed with H2O and brine, dried over Na2SO4,and concentrated in vacuo. The residue was purified by columnchromatography on silica gel (hexane/EtOAc = 17:3 to 3:2) and columnchromatography on amino functionalized silica gel (hexane/EtOAc = 9:1 to 7:3) to give the product (5.29 g, 96%) as a colorlesssolid. 1H NMR (DMSO-d6): d 1.19 (3H, t, J = 7.1 Hz), 3.64-3.79 (8H,m), 3.72 (2H, s), 4.10 (2H, q, J = 7.1 Hz), 7.25 (1H, d, J = 7.6 Hz),7.35-7.45 (1H, m), 7.50-7.58 (2H, m), 8.70 (2H, s); MS (ESI) m/z[M+H]+ 328. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | General procedure: Amine (1 mmol) and aldehyde (1 mmol) in 5 mL of absolute ethanol refluxed for 2 h. After that,ketone (2.5 mmol) and catalytic amount of conc. hydrochloric acid was added to the reaction mixture. The reaction mixture was continued to reflux for another 6-12 h. After completion, thereaction mixture was concentrated and purified by silica gel chromatography (Hexanes/ethylacetate 95:5 to 50:50) or dichloromethane/methanol (99:01 to 80:20) to give the desired cyclized compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: Amine (1 mmol) and aldehyde (1 mmol) in 5 mL of absolute ethanol refluxed for 2 h. After that,ketone (2.5 mmol) and catalytic amount of conc. hydrochloric acid was added to the reaction mixture. The reaction mixture was continued to reflux for another 6-12 h. After completion, thereaction mixture was concentrated and purified by silica gel chromatography (Hexanes/ethylacetate 95:5 to 50:50) or dichloromethane/methanol (99:01 to 80:20) to give the desired cyclized compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | General procedure: Amine (1 mmol) and aldehyde (1 mmol) in 5 mL of absolute ethanol refluxed for 2 h. After that,ketone (2.5 mmol) and catalytic amount of conc. hydrochloric acid was added to the reaction mixture. The reaction mixture was continued to reflux for another 6-12 h. After completion, thereaction mixture was concentrated and purified by silica gel chromatography (Hexanes/ethylacetate 95:5 to 50:50) or dichloromethane/methanol (99:01 to 80:20) to give the desired cyclized compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | General procedure: Amine (1 mmol) and aldehyde (1 mmol) in 5 mL of absolute ethanol refluxed for 2 h. After that,ketone (2.5 mmol) and catalytic amount of conc. hydrochloric acid was added to the reaction mixture. The reaction mixture was continued to reflux for another 6-12 h. After completion, thereaction mixture was concentrated and purified by silica gel chromatography (Hexanes/ethylacetate 95:5 to 50:50) or dichloromethane/methanol (99:01 to 80:20) to give the desired cyclized compound. |
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