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CAS No. : | 155377-05-2 | MDL No. : | MFCD02090527 |
Formula : | C8H6F3NO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | AYABEJGGSWJVPN-UHFFFAOYSA-N |
M.W : | 205.13 | Pubchem ID : | 45158822 |
Synonyms : |
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Chemical Name : | Methyl 6-(trifluoromethyl)picolinate |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
96% | With triethylamine;1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; at 60℃; for 17h; | Add palladium(II) acetate (200 mg, 2 w/w%) and l,l '-bis(diphenylphosphino)ferrocene (dppf) (400 mg, 4 w/w%) to a solution of 2-chloro-6-trifluoromethyl-pyridine (10.0 g, 55.1 mmol) in methanol (30 mL). To the orange solution add triethylamine (8.45 mL, 60.6 mmol). Purge the mixture with nitrogen and then maintain under an atmosphere of carbon monoxide (40 psig) at 60 0C for 17 h. Cool to ambient temperature and concentrate under a reduced pressure. Dissolve the solid in tert-butylmethyl ether (70 mL). Filter the resulting slurry over silica gel (10 g) and diatomaceous earth (10 g).Concentrate the filtrate to afford the title compound as a light orange solid (10.8 g, 96%). 1H NMR (399.84 MHz, DMSO d6): 8.31-8.27 (m, IH), 8.14 (dd, J= 2.4, 6.4 Hz, 2H), 3.91 (s, 3H). HRMS (ESI) m/z (M+H)+ calcd for C8H7F3NO2: 206.0423, found 206.0422. |
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine; at 60℃; for 22h; | Step 1: Preparation of 6-trifluomethyl-pyridine-2-carboxylic acid methyl ester (2) To a solution of 2-chloro-6-trifluoromethyl-pyridine (2 g, 11.1 mmol, 1.0 eq) in MeOH (20 mL) was add Pd(OAc)2 (124 mg, 0.05 eq) and dppf (600 mg, 0.1 eq) under an atmosphere of nitrogen. Et3N (2.3 mL, 1.5 eq) was then added to the resulting orange solution. The reaction solution was then stirred under an atmosphere of carbon monoxide (40 psi) at 60 C. for 22 hr. Once the reaction completed, the mixture was filtered and the filtrate was concentrated in high vacuum. The residue was purified by column chromatography to afford the desired product. 1HNMR (400 MHz, CDCl3): delta 8.32 (d, J=8 Hz, 1H), 8.06 (t, J=8 Hz, 1H), 8.88 (d, J=8 Hz, 1H), 4.04 (s, 3H). LC-MS: m/z 206 (M+H)+. | |
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine; In methanol; at 60℃; under 2068.65 Torr; for 22h;Inert atmosphere; | Step 1: Preparation of 6-trfluomethyl-pyridine-2-carboxylic acid methyl ester (2). To a solution of 2-chloro-6-trifluoromethyl-pyridine (2 g, 11.1 mmol, 1.0 eq) in MeOH (20 mL) was add Pd(OAc)2 (124 mg, 0.O5eq) and dppf (600 mg, 0.leq) under an atmosphere of nitrogen. Et3N (2.3 mL, 1 .5eq) was then added to the resulting orange solution. The reaction solution was then stirred under an atmosphere of carbon monoxide (40 psi) at 60C for 22 hr. Once the reaction completed, the mixture was filtered and the filtrate was concentrated in high vacuum. The residue was purified by column chromatography to afford the desired product.?HNMR (400 MHz, CDC13): 8.32 (d, J 8 Hz, 111), 8.06 (t, J= 8 Hz, 111), 8.88 (d, J= 8 Hz, 111), 4.04 (s, 3H).LC-MS: m/z 206 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Add -trifluoromethyl-pyridine^-carboxylic acid methyl ester (80.0 g, 390 mmol) to a mixture of THF (240 mL) and tert-butylmethyl ether (400 mL). Add the solution slowly to a 3 M methylmagnesium chloride in THF (390 mL, 1.17 moles) and maintain 8 0C to 16 0C. Cool the mixture to 0 0C and add a mixture of 5 M hydrochloric acid (257 mL, 1.29 moles) and water (200 mL). Separate the phases and concentrate the organic phase under reduced pressure. Add heptane (160 mL) and cool the mixture to 5 0C. Collect the precipitate by vacuum filtration and rinse the solid with heptane (20 mL) followed by pentane (30 mL). Vacuum dry the solid to afford the title compound as a tan solid (72.3 g, 352 mmol, 90 %). 1H NMR (400 MHz, DMSO d6) delta 8.04 (t, J= 7.7 Hz, IH), 7.94 (d, J= 7.9 Hz, IH), 7.69 (d, J= 7.0 Hz, IH), 5.40 (s, IH), 1.43 (s, 6H). HRMS (ESI) m/z (M+H)+ calcd for C9Hi0F3NO : 206.0787, found 206.0787. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 80℃; for 48h; | General procedure: Example 3, step 1: Preparation of 6-chloro-pyridine-2-carboxylic acid methyl ester (10). To a solution of 6-chloro-pyridine-2-carboxylic acid (48 g, 0.31 mol) in methanol (770 ml) was added concentrated HC1 (6 ml). The mixture was stirred at 80C for 48 hours then concentrated to remove the volatile. The crude product was diluted with ethyl acetated and washed with Sat. NaHCC"3 solution. The organic layer was dried with anhydrous Na2S04 and concentrated to give -chloro-pyridine-2-carboxylic acid methyl ester as a white solid. LC-MS: m/z 172.0 (M+H)+. | |
With hydrogenchloride; In water; at 80℃; for 48h; | General procedure: To a solution of 6-chloro-pyridine-2-carboxylic acid (48 g, 0.31 mol) in methanol (770 ml) was added concentrated HCl (6 ml). The mixture was stirred at 80C for 48 hours then concentrated to remove the volatile. The crude product was diluted with ethyl acetated and washed with Sat. NaHC03 solution. The organic layer was dried with anhydrous Na2S04 and concentrated to give 6-chloro-pyridine-2-carboxylic acid methyl ester as a white solid. LC-MS: m/z 172.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium; In ethanol; for 1h;Reflux; | Step 1: Preparation of 2-(6-Trifluoromethyl-pyridin-2-yl)-1H-pyrimidine-4, 6-dione To a solution of sodium (32 g, 0.16 mol) in ethanol (500 mL) was added 6-trifluoro- methylpyridine-2-carboxylic acid methyl ester (6.15 g, 3 mmol) and malonamide (1.02 g, 1 mmol). The mixture was heated to reflux for 1 hour, then concentrated to give a residue which was poured to water (100 mL). Saturated NaHCO3 solution was added to adjust to pH 7, the mixture was filtered, and then added iN HC1 solution to adjust pH to 3. DCM (20 mL) was added, and the precipitated solid was collected by filtration and dried to give 2-(6-trifluoromethyl-pyridin-2-yl)- 1 H-pyrimidine-4,6-dione. LCMS: [M+ 1] = 257.9 |
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