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[ CAS No. 53277-47-7 ]

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Chemical Structure| 53277-47-7
Chemical Structure| 53277-47-7
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CAS No. :53277-47-7 MDL No. :MFCD11845763
Formula : C8H8ClNO2 Boiling Point : 252.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :185.61 g/mol Pubchem ID :13055804
Synonyms :

Safety of [ 53277-47-7 ]

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:

Application In Synthesis of [ 53277-47-7 ]

  • Upstream synthesis route of [ 53277-47-7 ]
  • Downstream synthetic route of [ 53277-47-7 ]

[ 53277-47-7 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
99%
Stage #1: With oxalyl dichloride In dichloromethane for 0.5 h;
Stage #2: at 0 - 20℃;
The starting material, 5-[5-(3,5-bistrifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-indolizine-8-carboxylic acid, was prepared as follows: a. Oxalyl chloride (9.3 mL) was added to a solution of 2-chloro-6-methyl-nicotinic acid (9 g) in DCM (500 mL). After stirring 30 minutes, the mixture was concentrated under reduced pressure to give a residue that was treated with MeOH (500 mL) at 0° C. After stirring overnight at room temperature, the mixture was concentrated under reduced pressure to give a residue that was diluted with water and EA, neutralized with a saturated aqueous solution of sodium bicarbonate solution and extracted three times with EA. The organic layer was collected, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 2-chloro-6-methyl-nicotinic acid methyl ester (9.7 g, 99percent). 1H NMR (400 MHz, CHLOROFORM-d): 2.60 (s, 3H), 3.95 (s, 3H), 7.17 (d, J=7.8 Hz, 1H), 8.09 (d, J=7.8 Hz, 1H).
93% With diazomethyl-trimethyl-silane In tetrahydrofuran; methanol; diethyl ether at 20℃; A 2 M ether solution of (trimethylsilyl)diazomethane (30 mL, 60.0 mmol) was added to a solution of 2-chloro-6-methylnicotinic acid (8 g, 45.2 mmol) in TηF (100 mL) and MeOH (25 mL) in a room temperature water bath. After 30 min, ηOAc (2 mL) was added. The mixture was concentrated and purified by silica gel chromatography, eluting with 0-20percent EtOAc in hexanes, to give methyl 2-chloro-6- methylnicotinate as colorless oil (7.77 g, 93percent yield). MS (ES+) m/z: 186 (M+η); LC retention time: 2.64 min (analytical ηPLC Method A).
Reference: [1] Patent: US2011/152312, 2011, A1, . Location in patent: Page/Page column 35
[2] Patent: WO2009/100171, 2009, A1, . Location in patent: Page/Page column 82
[3] Patent: US2010/144760, 2010, A1, . Location in patent: Page/Page column 30; 31
[4] Patent: WO2010/72722, 2010, A1, . Location in patent: Page/Page column 50
[5] Patent: WO2006/25783, 2006, A1, . Location in patent: Page/Page column 65-66
[6] Patent: US2006/89392, 2006, A1, . Location in patent: Page/Page column 38
[7] Patent: WO2014/176144, 2014, A1, . Location in patent: Page/Page column 46-47
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YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In DMF (N,N-dimethyl-formamide) for 18 h; The first step
of Scheme 11:
To a stirred solution of 2-chloro-6-methyl-nicotinic acid (13.6 g, 80 mmol) in DMF (118 mL) was added potassium carbonate (30 g, 219 mmol) and methyl iodide (23 mL, 366 mmol).
After 18 hours, the reaction was diluted with ethyl acetate (300 mL) and washed with water (200 mL).
The organic layer was dried over magnesium sulfate and filtered.
The solvent was removed under reduced pressure.
The material was loaded on silica gel and filtered through a buchner funnel eluding with 1:1 ethyl acetate to yield 14.8 g (99percent) of 2-chloro-6-methyl-nicotinic acid methyl ester as a light orange liquid.
1H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.59 (s, 3H) 3.94 (s, 3H) 7.16 (d, J=7.83 Hz, 1H) 8.09 (d, J=7.83 Hz, 1H).
94% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h; [409] Step A: 2-chloro-6-methyl-nicotinic acid methyl ester [410] 2-Chloro-6-methyl-nicotinic acid (3.58 g, 20.86 mmol) was dissolved in DMF(34 mL). MeI (5.8 mL, 93.88 mmol) and K2CO3 (7.78 g,56.33 mmol) were added thereto, and the mixture was stirred at room temperaturefor 2 hours. The reactant was distilled under reduced pressure to remove thesolvent and extracted with EtOAc. The organic layer was dried with MgSO4,filtered and concentrated under reduced pressure. The obtained residue waspurified by column chromatography (eluent EtOAc/Hex = 1/2) to obtain the titlecompound (3.68 g, 94percent).[411] NMR: 1H-NMR (CDCl3) 8.08(1H, d), 7.16(1H, d),3.92(3H, s), 2.57(3H, s)
Reference: [1] Patent: US2005/203081, 2005, A1, . Location in patent: Page/Page column 12; 30
[2] Patent: WO2014/69963, 2014, A1, . Location in patent: Paragraph 409-411
[3] Patent: US6342765, 2002, B1, . Location in patent: Page column 53-54
[4] Patent: EP2248423, 2010, A1, . Location in patent: Page/Page column 269-270
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YieldReaction ConditionsOperation in experiment
92% With potassium carbonate; methyl iodide In N,N-dimethyl-formamide at 20℃; for 3 h; To a stirred solution of 2-chloro-6-methyl-pyridine-3-carboxylic acid (1 g, 5.83 mmol) in DMF (4 mL) was added K2C03 (2.2 g, 15.74 mmol) and CH3I (3.7 g, 26.23 mmol, 1.6 mL) at 20 °C. The reaction mixture was stirred at 20 °C for 3 hrs. The reaction was diluted with water (40 mL) and extracted with EtOAc. The combined organic layers were dried over Mg504, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford methyl 2-chloro-6- methyl-pyridine-3-carboxylate (1 g, 92 percent yield) as a white solid. ‘H NMR (400 IVIFIz, Methanol-d4) ppm 8.13 (d, J=7.89 Hz, 1 H) 7.49 -7.22 (m, 1 H) 3.91 (s, 3 H) 2.54 (s, 3 H). LCMS (ESI): m/z [M +H] calculated for C8H9C1NO2: 186.0; found 186.1.
Reference: [1] Patent: WO2018/136264, 2018, A1, . Location in patent: Paragraph 00490
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 6, p. 996 - 1001
[3] Patent: WO2011/75591, 2011, A1,
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YieldReaction ConditionsOperation in experiment
99% at 0℃; a. Oxalyl chloride (9.3 mL) was added to a solution of 2-chloro-6-methyl-nicotinic acid (9 g) in DCM (500 mL). After stirring 30 minutes, the mixture was concentrated under reduced pressure to give a residue that was treated with MeOH (500 mL) at 0°C. After stirring overnight at room temperature, the mixture was concentrated under reduced pressure to give a residue that was diluted with water and EA, neutralized with a saturated aqueous solution of sodium bicarbonate solution and extracted three times with EA. The organic layer was collected, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 2-chloro-6-methyl-nicotinic acid methyl ester (9.7 g, 99percent). 1H NMR (400 MHz, CHLOROFORM-d): 2.60 (s, 3H), 3.95 (s, 3H), 7.17 (d, J=7.8 Hz, 1H), 8.09 (d, J=7.8 Hz, 1H).
Reference: [1] Patent: WO2011/75591, 2011, A1, . Location in patent: Page/Page column 84
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Reference: [1] Patent: WO2010/122151, 2010, A1, . Location in patent: Page/Page column 52
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Reference: [1] Patent: US2004/38962, 2004, A1,
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Reference: [1] Patent: WO2015/35113, 2015, A1, . Location in patent: Page/Page column 78; 79
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Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 6, p. 996 - 1001
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Reference: [1] Patent: US2010/144760, 2010, A1, . Location in patent: Page/Page column 31
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