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CAS No. : | 1416721-24-8 | MDL No. : | MFCD18757662 |
Formula : | C14H16BF3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SXGHUSPRZSUDTF-UHFFFAOYSA-N |
M.W : | 300.08 | Pubchem ID : | 74789443 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 73.31 |
TPSA : | 35.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.82 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.25 |
Log Po/w (WLOGP) : | 3.97 |
Log Po/w (MLOGP) : | 1.96 |
Log Po/w (SILICOS-IT) : | 3.09 |
Consensus Log Po/w : | 2.45 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.76 |
Solubility : | 0.052 mg/ml ; 0.000173 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.67 |
Solubility : | 0.0642 mg/ml ; 0.000214 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.82 |
Solubility : | 0.00453 mg/ml ; 0.0000151 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.01 |
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 |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane / 4 h / 20 °C 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 8-amino quinoline / tetrahydrofuran / 12 h / 90 °C / Glovebox |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With 8-amino quinoline; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In tetrahydrofuran at 90℃; for 12h; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (η6-1,3,5-cyclooctatriene)(η4-1,5-cyclooctadiene)ruthenium(0) / tetrahydrofuran / 24 h / 120 °C / Inert atmosphere; Schlenk technique 2: hydrogenchloride; water / tetrahydrofuran / 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; water In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; | General Procedure for Catalytic Borylation of Aromatic Imines General procedure: Ru(cod)(cot) (1.6 mg, 5.0 μmol) were placed in a resealable Schlenk tube. The tube was evacuatedand backfilled with nitrogen, and then charged with THF (0.5 mL), an imine 2 (0.250 mmol), and pinacolborane (1; 72 μL, 0.50 mmol). The reaction mixture was then stirred at 120 °C for 24 h. The resulting mixture was allowed to cool to room temperature, 0.5 M hydrochloric acid (1.0 mL) was added. After vigorous shaking and mixing, the mixture was diluted with ether, washed with brine, and dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (boric-acid-impregnated silica gel) to afford the desired product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80℃;Inert atmosphere; | A 500-mL round-bottom flask was charged with <strong>[85118-24-7]2-bromo-4-(trifluoromethyl)benzaldehyde</strong> (10.1 g, 39.9 mmol, 1.00 equiv), 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (15.3 g, 60.3 mmol, 1.50 equiv), 1,1'-bis(diphenylphosphino)ferrocenepalladiumdichloride (1.47 g, 2.01 mmol, 0.05 equiv), potassium acetate (11.8 g, 121 mmol, 3.00 equiv), and dimethyl sulfoxide (100 mL) under nitrogen. The resulting solution was allowed to stir overnight at 80 C. before quenching with water (100 mL). The mixture was extracted with ethyl acetate (3*100 mL) and the organic layers were combined, washed with brine (2*100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/5) to provide 5.00 g (42% yield) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 2 h / 20 °C 2.2: 20 °C 3.1: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: potassium carbonate / acetonitrile / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C 2.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 2: triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 2: triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C 3: lithium hydroxide; water / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 2: triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C 3: lithium hydroxide; water / tetrahydrofuran / 20 °C 4: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 1 h / 20 °C 3.1: lithium hydroxide; water / tetrahydrofuran / 20 °C 4.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C 5.2: 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 2 h / 20 °C 2.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 2 h / 20 °C 2.2: 20 °C 3.1: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 2 h / 20 °C 2.2: 20 °C 3.1: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; | 3.3 Step 3: Synthesis of tert-butyl 2-(3-(2-formyl-5-(trifluoromethyl)phenyl)-1H-pyrazol-1-yl)acetate A 40-mL round-bottom flask was charged with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (400 mg, 1.33 mmol, 1.00 equiv), tert-butyl 2-(3-bromo-1H-pyrazol-1-yl)acetate (520 mg, 1.99 mmol, 1.50 equiv), tetrakis(triphenylphosphine)palladium (80.9 mg, 0.0700 mmol, 0.05 equiv), potassium carbonate (552 mg, 3.99 mmol, 3.00 equiv), 1,4-dioxane (10 mL), and water (2 mL) under nitrogen. The resulting solution was allowed to stir overnight at 80° C. before quenching with water (10 mL). The mixture was then extracted with ethyl acetate (3*10 mL) and the organic layers were combined, washed with brine (2*10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/4) to provide 55.0 mg (12% yield) of tert-butyl 2-(3-(2-formyl-5-(trifluoromethyl)phenyl)-1H-pyrazol-1-yl)acetate as a yellow oil. LCMS (ESI, m/z): 355 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere; | A 40-mL round-bottom flask was charged with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (300 mg, 1.00 mmol, 1.00 equiv), <strong>[76360-43-5]methyl 2-bromothiophene-3-carboxylate</strong> (330 mg, 1.49 mmol, 1.50 equiv), tetrakis(triphenylphosphine)palladium (57.8 mg, 0.0500 mmol, 0.05 equiv), potassium carbonate (414 mg, 3.00 mmol, 3.00 equiv), 1,4-dioxane (10 mL), and water (2 mL) under nitrogen. The resulting solution was stirred overnight at 80 C. before quenching with water (10 mL). The mixture was extracted with ethyl acetate (3*10 mL) and the organic layers were combined, washed with brine (2*10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/4) to provide 100 mg (32% yield) of methyl 2-(2-formyl-5-(trifluoromethyl)phenyl)thiophene-3-carboxylate as a yellow oil. LCMS (ESI, m/z): 315 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water Inert atmosphere; | 2.5 Step 5: Synthesis of tert-butyl 3-(2-formyl-5-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate A 50-mL round-bottom flask was charged with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (400 mg, 1.33 mmol, 1.00 equiv) in 1,4-dioxane/water (10/2 mL), tert-butyl 3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate (422 mg, 1.33 mmol, 1.10 equiv), tetrakis(triphenylphosphine)Palladium (77.0 mg, 0.0700 mmol, 0.05 equiv), and potassium carbonate (552 mg, 3.99 mmol, 3.00 equiv) under nitrogen. The reaction mixture was allowed to stir overnight at 80° C. before quenching with water (20 mL). The resulting solution was extracted with ethyl acetate (3*20 mL) and the organic layers were combined, washed with brine (2*20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/3) to provide 400 mg (88% yield) of tert-butyl 3-(2-formyl-5-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate as a yellow oil. LCMS (ESI, m/z): 286 [M+H-56]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / Inert atmosphere 2.1: triethylamine / 1,2-dichloro-ethane / 2 h / 20 °C 2.2: 20 °C 3.1: hydrogen; palladium on activated charcoal / ethyl acetate / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: potassium carbonate / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.81% | With ammonium hydroxide In ethanol at 25 - 50℃; for 1h; | 19.2; 49.2 Step 2: To a mixture of (3-methylsulfanylphenyl)hydrazine (100 mg, 648.37 umol, 1 eq) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (200 mg, 666.49 umol, 1.03 eq) in EtOH (3 mL) was added NH3.H2O (182 mg, 1.30 mmol, 0.2 mL, 25% purity, 2.00 eq) in one portion at 25 °C, the mixture was heated to 50 °C and stirred for 1 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by Prep-HPLC (column: Nano-micro Kromasil C18100*30mm 5um;mobile phase: [water(0.1%TFA)-ACN];B%: 55%-80%,10 min) to give 1-hydroxy-2-(3-methyl sulfanylphenyl)-7- (trifluoromethyl)-2,3,1-benzodiazaborinine (106 mg, 303.52 umol, 46.81% yield, 96.25% purity) as a gray solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.36 (s, 1H), 8.85 (s, 1H), 8.35 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 8.05 (d, J = 8.4 Hz, 1H), 7.47 (s, 1H), 7.37 (d, J = 4.8 Hz, 2H), 7.16-7.14 (m, 1H), 2.50 (s, 3H). MS (ESI): mass calcd. For C15H12BF3N2OS 336.07, m/z found 337.1 [M+H]+. HPLC: 96.25% (220 nm), 97.85% (254 nm). |
46.81% | With ammonium hydroxide In ethanol at 25 - 50℃; for 1h; | 19.2; 49.2 Step 2: To a mixture of (3-methylsulfanylphenyl)hydrazine (100 mg, 648.37 umol, 1 eq) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (200 mg, 666.49 umol, 1.03 eq) in EtOH (3 mL) was added NH3.H2O (182 mg, 1.30 mmol, 0.2 mL, 25% purity, 2.00 eq) in one portion at 25 °C, the mixture was heated to 50 °C and stirred for 1 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by Prep-HPLC (column: Nano-micro Kromasil C18100*30mm 5um;mobile phase: [water(0.1%TFA)-ACN];B%: 55%-80%,10 min) to give 1-hydroxy-2-(3-methyl sulfanylphenyl)-7- (trifluoromethyl)-2,3,1-benzodiazaborinine (106 mg, 303.52 umol, 46.81% yield, 96.25% purity) as a gray solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.36 (s, 1H), 8.85 (s, 1H), 8.35 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 8.05 (d, J = 8.4 Hz, 1H), 7.47 (s, 1H), 7.37 (d, J = 4.8 Hz, 2H), 7.16-7.14 (m, 1H), 2.50 (s, 3H). MS (ESI): mass calcd. For C15H12BF3N2OS 336.07, m/z found 337.1 [M+H]+. HPLC: 96.25% (220 nm), 97.85% (254 nm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.73% | With ammonium hydroxide In ethanol at 25 - 50℃; for 2h; | 118.2 Step 2: To a mixture of (3,4,5-trichlorophenyl)hydrazine (200 mg, 946 umol, 1.04 eq) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (300 mg, 999 umol, 1.1 eq) in EtOH (5 mL) was added NH3.H2O (273 mg, 1.95 mmol, 0.3 mL, 25% purity, 2.14 eq) in one portion at 25 °C. The mixture was heated to 50 °C and stirred for 2 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by Prep-HPLC (column: Welch Xtimate C18100*25mm*3um;mobile phase: [water(0.1%TFA)-ACN];B%: 55%-85%,12min) to give 1-hydroxy-2-(3,4,5-trichlorophenyl) -7- (trifluoromethyl)-2,3,1-benzodiazaborinine (117 mg, 297 umol, 32.73% yield, 100% purity) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.84 (s, 1H), 8.83 (s, 1H), 8.39 (s, 1H), 8.10-8.07 (m, 1H), 8.05-8.03 (m, 1H), 7.96 (s, 2H). MS (ESI): mass calcd. For C14H7BCl3F3N2O 391.97, m/z found 394.9 [M+H]+. HPLC: 100% (220 nm), 100% (254 nm). |
32.73% | With ammonium hydroxide In ethanol at 25 - 50℃; for 2h; | 118.2 Step 2: To a mixture of (3,4,5-trichlorophenyl)hydrazine (200 mg, 946 umol, 1.04 eq) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzaldehyde (300 mg, 999 umol, 1.1 eq) in EtOH (5 mL) was added NH3.H2O (273 mg, 1.95 mmol, 0.3 mL, 25% purity, 2.14 eq) in one portion at 25 °C. The mixture was heated to 50 °C and stirred for 2 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by Prep-HPLC (column: Welch Xtimate C18100*25mm*3um;mobile phase: [water(0.1%TFA)-ACN];B%: 55%-85%,12min) to give 1-hydroxy-2-(3,4,5-trichlorophenyl) -7- (trifluoromethyl)-2,3,1-benzodiazaborinine (117 mg, 297 umol, 32.73% yield, 100% purity) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.84 (s, 1H), 8.83 (s, 1H), 8.39 (s, 1H), 8.10-8.07 (m, 1H), 8.05-8.03 (m, 1H), 7.96 (s, 2H). MS (ESI): mass calcd. For C14H7BCl3F3N2O 391.97, m/z found 394.9 [M+H]+. HPLC: 100% (220 nm), 100% (254 nm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.41% | With ammonium hydroxide In ethanol at 25 - 50℃; for 1h; | 21.6; 71.6 Step 6: To a mixture of [3-(trifluoromethylsulfanyl)phenyl]hydrazine (200 mg, 960.60 umol, 1.06 eq) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4- (trifluoromethyl)benzaldehyde (300 mg, 999.73 umol, 1.1 eq) in EtOH (5 mL) was added NH3.H2O (273 mg, 1.95 mmol, 0.3 mL, 25% purity, 2.14 eq) in one portion at 25 °C, the mixture was heated to 50 °C and stirred for 1 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by Prep-HPLC (column: Welch Xtimate C18 150*25mm*5um;mobile phase: [water(10mM NH4HCO3)-ACN];B%: 75%-95%,10.5min) to give 1-hydroxy-7- (trifluoromethyl)-2-[3-(trifluoromethylsulfanyl)phenyl]-2,3,1-benzodiazaborinine (48 mg, 121.91 umol, 13.41% yield, 99.08% purity) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.61 (s, 1H), 8.86 (s, 1H), 8.40 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.98 (s, 1H), 7.90-7.88 (m, 1H), 7.60(d, J = 6.4 Hz, 2H). MS (ESI): mass calcd. For C15H9BF6N2OS 390.04, m/z found 391.0 [M+H]+. HPLC: 99.08% (220 nm), 98.64% (254 nm). |
13.41% | With ammonium hydroxide In ethanol at 25 - 50℃; for 1h; | 21.6; 71.6 Step 6: To a mixture of [3-(trifluoromethylsulfanyl)phenyl]hydrazine (200 mg, 960.60 umol, 1.06 eq) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4- (trifluoromethyl)benzaldehyde (300 mg, 999.73 umol, 1.1 eq) in EtOH (5 mL) was added NH3.H2O (273 mg, 1.95 mmol, 0.3 mL, 25% purity, 2.14 eq) in one portion at 25 °C, the mixture was heated to 50 °C and stirred for 1 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by Prep-HPLC (column: Welch Xtimate C18 150*25mm*5um;mobile phase: [water(10mM NH4HCO3)-ACN];B%: 75%-95%,10.5min) to give 1-hydroxy-7- (trifluoromethyl)-2-[3-(trifluoromethylsulfanyl)phenyl]-2,3,1-benzodiazaborinine (48 mg, 121.91 umol, 13.41% yield, 99.08% purity) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.61 (s, 1H), 8.86 (s, 1H), 8.40 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.98 (s, 1H), 7.90-7.88 (m, 1H), 7.60(d, J = 6.4 Hz, 2H). MS (ESI): mass calcd. For C15H9BF6N2OS 390.04, m/z found 391.0 [M+H]+. HPLC: 99.08% (220 nm), 98.64% (254 nm). |
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