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CAS No. : | 196083-18-8 | MDL No. : | MFCD04038223 |
Formula : | C8H5BF6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CVZMLRIREADJRS-UHFFFAOYSA-N |
M.W : | 257.93 g/mol | Pubchem ID : | 2779084 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
33% | With triethylamine;copper diacetate; In 1,2-dichloro-ethane; at 50.0℃; for 2h; | Step 1: N'-(2,5-Bis-trifluoromethyl-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 600 mg, 3.4 mmol), <strong>[196083-18-8]2,5-bis(trifluoromethyl)phenylboronic acid</strong> (ChemFocus, LLC, East Brunswick, N.J., USA; 953 mg, 3.7 mmol), copper(II) acetate (746 mg, 4.1 mmol) and triethylamine (575 μL, 4.1 mmol) in 1,2-dichloroethane (18 mL) was heated in an oil bath at 50 C. for 2 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluding with 10% ethyl acetate/hexanes, to give N'-(2,5-bis-trifluoromethyl-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (480 mg, 33%) as a colorless oil that solidified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With iron(III) chloride; water; In tetrahydrofuran; at 65.0℃; for 7h; | General procedure: Potassium phenyltrifluoroborate (184 mg, 1.00 mmol) was added to a solution of iron trichloride (185 mg, 1.10 mmol) in 3 mL of 1:1 THF/water. The mixture was stirred at room temperature for 30 min. The reaction mixture was then passed through a short column containing neutral absorption alumina. The alumina was then washed with a mixture of ethyl acetate/hexanes (2:1) to obtain phenylboronic acid (105 mg, 86%). [The boronic acid products can also be isolated by simple extraction techniques.] All products possessed physical and spectral characteristics (13C, 1H, 11B NMR) in accord with literature values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; lithium chloride; In ethanol; water; toluene; at 100.0℃; for 5h;Inert atmosphere; | General procedure: Ethyl cyanoacetate (5.3mL, 50mmol) was added to a suspension of sodium (1.15g, 50mmol) in 150mL of anhydrous EtOH at 0C. After 20min at room temperature, the reaction mixture was concentrated and the resultant solid was added to a solution of 1-(2-aminopyrimidin-4-yl)-2-bromoethanone hydrobromide (35, 14.85g, 50mmol) and N,N-diisopropylethylamine (8.8mL, 50mmol) in anhydrous THF (300mL). The reaction mixture was stirred overnight at room temperature, concentrated and the residue was suspended in water and extracted with DCM. The organic extracts were dried over sodium sulfate and concentrated. The crude was purified by flash chromatography (DCM/MeOH 95:5) to give ethyl 4-(2-aminopyrimidin-4-yl)-2-cyano-4-oxobutanoate (36, 5.16 g, 41%). 1H NMR (400MHz, DMSO-d6) δ 8.52 (d, J=4.9Hz, 1H), 6.97 (d, J=4.9Hz, 1H), 4.56 (t, J=5.6Hz, 1H), 4.19 (q, J=7.1Hz, 2H), 3.74 (d, J=5.6Hz, 2H), 1.21 (t, J=7.1Hz, 3H); LC-MS (ESI): m/z 249 [M+H]+; HRMS (ESI): m/z calcd for C11H12N4O3+H+ 249.0982, found 249.0975. A suspension of 36 (5.0g, 20.14mmol) in DCM (40mL) was added dropwise to 33% HBr in AcOH (40mL) at 0C. The mixture was left at 0C for 30min and then at room temperature until disappearance of the starting material. The solid was filtered, washed with DCM, neutralized with 7N NH3 in MeOH to afford ethyl 5-(2-aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxylate (37, 5.5g, 88%). 1H NMR (400MHz, DMSO-d6) δ 12.84 (br s, 1H), 8.22 (d, J=5.4Hz, 1H), 7.23 (s, 1H), 6.99 (d, J=5.1Hz, 1H), 6.42 (br s, 2H), 4.21 (q, J=7.1Hz, 2H), 1.29 (t, J=7.1Hz, 3H); LC-MS (ESI): m/z 312 [M+H]+; HRMS (ESI): m/z calcd for C11H11BrN4O2+H+ 311.0138, found 311.0139. To a solution of 37 (2.0g, 6.43mmol) dissolved in EtOH (20mL) and toluene (20mL), LiCl (408mg, 9.64mmol), 1M aq Na2CO3 (17mmol), 5-chloro-2-methylphenylboronic acid (1.423g, 8.35mmol) were added. The resulting reaction mixture was degassed three times back filling with argon each time before being charged with Pd(Ph3P)2Cl2 (470mg, 0.67mmol), degassed four times back filling with argon each time and then heated at 100C for 5h. After cooling to room temperature, the precipitate was filtered and the filtrate was evaporated under reduced pressure, dissolved in DCM and washed with water. The organic layer was then dried over sodium sulfate and concentrated. The crude material was chromatographed on silica gel (DCM/EtOAc 50:50) to afford ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxylate (38e, 1.99g, 87%). 1H NMR (400MHz, DMSO-d6) δ 12.18 (br s, 1H), 8.21 (d, J=5.2Hz, 1H), 7.40 (dd, J=8.2, 2.2Hz, 1H), 7.27-7.34 (m, 3H), 7.01 (d, J=5.2Hz, 1H), 6.41 (s, 2H), 4.04 (q, J=7.1Hz, 2H), 2.11 (s, 3H), 1.09 (t, J=7.1Hz, 3H); LC-MS (ESI): m/z 357 [M+H]+; HRMS (ESI): m/z calcd for C18H17ClN4O2+H+ 357.1113, found 357.1115. The intermediate 38e (1.0g, 2.80mmol) was treated with 1.5M KOH in 95% EtOH (37.3mL, 20equiv) under reflux for 20h. After cooling, the residue was concentrated, dissolved in water and washed with DCM. A solution of 2N HCl was added, under agitation, to the aqueous phase cooled to 5C. The resultant precipitate was collected by filtration to give 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxylic acid (39e, 0.92g, 95%). 1H NMR (400MHz, DMSO-d6) δ 12.54 (br s, 1H), 12.06 (s, 1H), 8.28 (d, J=6.5Hz, 1H), 7.77 (br s, 1H), 7.59 (d, J=2.6Hz, 1H), 7.40-7.45 (m, 1H), 7.28-7.37 (m, 3H), 2.12 (s, 3H); LC-MS (ESI): m/z 329 [M+H]+; HRMS (ESI): m/z calcd for C16H13ClN4O2+H+ 329.0800, found 329.0799. A solution of 39e (470mg, 1.43mmol) in DMF/ THF (1/1, 5mL) and N,N-diisopropylethylamine (1.02mL, 5.86mmol) was stirred at 0C. EDCI (594mg, 3.1mmol) and HOBT·NH3 (430mg, 2.79mmol) were added and the reaction mixture was stirred for 3h at room temperature. The mixture was dropped into a saturated solution of NaHCO3 and ice and the resulting precipitate was collected by filtration to afford 6 (384mg, 82%). 1H NMR (400MHz, DMSO-d6) δ 11.84 (br s, 1H), 8.19 (d, J=5.2Hz, 1H), 7.32-7.40 (m, 2H), 7.26-7.30 (m, 2H), 7.22 (br s, 1H), 6.93 (d, J=5.2Hz, 1H), 6.73 (br s, 1H), 6.32 (br s, 2H), 2.12 (s, 3H); LC-MS (ESI): m/z 328 [M+H]+; HRMS (ESI): m/z calcd for C16H14ClN5O+H+ 328.0960, found 328.0959. The following compounds 2-5, and 25-34 were prepared according to the method described above using the suitable aryl boronic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.7% | (2,5-(Ditrifluoromethyl)phenyl)boronic acid (52 mmol) was dissolved in 1,4-dioxane (62 mL), KF (150 mmol) was added thereto, and the mixture was stirred for 1 hour.Then, Pd(OAc)2 (5mmol) was added and dissolved in 1,4-dioxane (62mL)2-bromo-5-(piperidin-4-ylmethyl)-4,5-dihydrothiazolo[5,4-c]quinoline (50mmol) in the mixture was added dropwise to the system, and the reaction mixture was stirred at room temperature 20 hours,It was then filtered through silica gel and washed with Et2O (65 mL). The solvent was removed by rotary evaporation and flash column chromatography (eluent was ethyl acetate) to obtain an off-white solid 5-(piperidin-4-ylmethyl)-2-(2,5-(ditrifluoromethyl) )Phenyl)-4,5-dihydrothiazolo[5,4-c]quinoline, 22.56g, yield 90.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrakis(triphenylphosphine) palladium(0); barium hydroxide octahydrate; In 1,4-dioxane; water; at 100.0℃; for 24h; | 3,5-Dibromophenyltrimethylsilane (0.85 g, 2.75 mmol), Ba(OH)28H2O(3.0 g, 9.60 mmol), <strong>[196083-18-8]2,5-bis(trifluoromethyl)phenylboronic acid</strong> (2.86 g, 11.0mmol),5 and Pd(PPh3)4 (0.26 g, 0.22 mmol) were mixed in dioxane/H2O (5/1)(48 mL). The mixture was stirred at 100 C. After 24 h, the reaction mixturewas quenched with 1N HCl, extracted with CH2Cl2. The combined organiclayer was washed with H2O and brine, dried over Na2SO4, and evaporated.The crude product was purified by column chromatography (hexane) to giveS1’ (1.4 g, 89 %). white solid; m.p. 98-108 C; 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 8.3 Hz, 2H), 7.78 (d, J = 8.3 Hz, 2H), 7.62 (s, 2H), 7.56 (d, J = 1.4Hz, 2H), 7.24 (s, 1H), 1.53 (s, 9H); 13C NMR (101 MHz, CDCl3) δ 140.0, 139.7,133.8 (q, J = 33.2 Hz), 132.0 (q, J = 30.8 Hz), 131.8, 128.7 (q, J = 3.9 Hz),128.2, 127.1 (q, J = 4.6 Hz), 125.2 (q, J = 3.7 Hz), 123.1 (q, J = 274.1 Hz), 0.0;19F NMR (376 MHz, CDCl3) δ 57.5, 63.19; HRMS (FD+) m/z calcd forC25H18F12Si [M]+ 574.09861, found 574.09898,. |
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