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[ CAS No. 153034-94-7 ]

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Chemical Structure| 153034-94-7
Chemical Structure| 153034-94-7
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Product Details of [ 153034-94-7 ]

CAS No. :153034-94-7 MDL No. :MFCD03095297
Formula : C6H5FIN Boiling Point : 244.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :237.01 g/mol Pubchem ID :10060052
Synonyms :

Safety of [ 153034-94-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153034-94-7 ]

  • Upstream synthesis route of [ 153034-94-7 ]
  • Downstream synthetic route of [ 153034-94-7 ]

[ 153034-94-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 2369-19-9 ]
  • [ 153034-94-7 ]
YieldReaction ConditionsOperation in experiment
109.69 g
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75 - -73℃; for 3.5 h; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran; hexane at -75℃; for 1.91667 h; Inert atmosphere
Diisopropylamine (92 mL) was added to THF (1.2 L), and the mixture was cooled to −18° C. under a nitrogen atmosphere. To this solution was added dropwise a solution (224 mL) of 2.69 M n-butyllithium in hexane. After the dropwise addition, the temperature was increased to −5° C. over 20 minutes while stirring this mixture. The reaction solution was cooled to −73° C. To this reaction solution was added dropwise a THF solution (240 mL) of 2-fluoro-5-methylpyridine (61 g). The reaction mixture was stirred at −75° C. for three and a half hours. To this reaction solution was added dropwise a THF solution (24 mL) of iodine (139 g). The reaction mixture was stirred at −75° C. for 1 hour and 55 minutes. After the reaction, water (220 mL) was added to the reaction solution at the same temperature. The mixture was stirred at the same temperature for 5 minutes. The reaction solution was brought back to room temperature, and then water (1.2 L) was added. To this mixture were added an aqueous solution (300 mL) of sodium thiosulfate pentahydrate (136 g) and water (300 mL), and the mixture was stirred for 10 minutes. This mixture was extracted with MTBE (1.2 L). The organic layer was washed with saturated saline (500 mL). The combined aqueous layers were extracted with MTBE (1 L). The combined organic layers were dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. n-Heptane was added to the residue, and the mixture was cooled. The precipitated solid was collected by filtration. The solid was washed with n-heptane. The filtrate was cooled, and the precipitated solid was collected by filtration. The procedure was repeated 5 times to give the title compound (109.69 g). (0167) 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.29-2.31 (m, 3H), 7.93-8.14 (m, 2H). (0168) ESI-MS m/z 238 [M+H]+
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 18, p. 4603 - 4606
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Patent: US2016/46623, 2016, A1, . Location in patent: Paragraph 0166-0168
  • 2
  • [ 153034-78-7 ]
  • [ 153034-94-7 ]
YieldReaction ConditionsOperation in experiment
87% With n-butyllithium; diisopropylamine In tetrahydrofuran A solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78° C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether.
The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 6.3 g (87percent) of the desired product. MS (DCI/NH3) m/z 238 (M+H)+; 1H NMR (CDCl3) δ7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).
87% With n-butyllithium; diisopropylamine In tetrahydrofuran A solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78° C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether.
The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 6.3 g (87percent) of the desired product. MS (DCI/NH3) m/z 238 (M+H)+; 1H NMR (CDCl3) δ 7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 18, p. 4603 - 4606
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Patent: US2003/87940, 2003, A1,
[4] Patent: US2002/115640, 2002, A1,
  • 3
  • [ 153034-94-7 ]
  • [ 1227581-81-8 ]
YieldReaction ConditionsOperation in experiment
27% With ammonium hydroxide In water; dimethyl sulfoxide at 140℃; for 4 h; Microwave irradiation A white suspension of 2-fluoro-4-iodo-5-methylpyridine (3.00 g, 12.7 mmol) and concentrated aqueous ammonium hydroxide (3.5 mL, 90 mmol) in DMSO (17 mL) was subjected to microwave conditions (140° C., 4 h) and then cooled. The reaction was diluted with EtOAc and water, and the layers were separated. The aqueous layer was extracted with EtOAc (3×50 mL), and the combined organic layers were concentrated under reduced pressure. The resulting residue was adsorbed onto silica gel and purified by flash silica chromatography, elution gradient 0 to 10percent MeOH in DCM, to afford 4-iodo-5-methylpyridin-2-amine (800 mg, 27percent) as a white solid. 1H NMR (300 MHz, DMSO-d6, 27° C.) 2.13 (s, 3H) 5.81 (s, 2H) 6.99 (s, 1H) 7.75 (s, 1H). m/z: ES+[M+H]+ 235.
Reference: [1] Patent: US2016/376287, 2016, A1, . Location in patent: Paragraph 0957
[2] Patent: WO2011/26904, 2011, A1, . Location in patent: Page/Page column 131
[3] Patent: WO2012/87519, 2012, A1, . Location in patent: Page/Page column 122
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