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[ CAS No. 153034-80-1 ]

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Chemical Structure| 153034-80-1
Chemical Structure| 153034-80-1
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CAS No. :153034-80-1 MDL No. :MFCD03095289
Formula : C6H5FIN Boiling Point : 244°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :237.01 g/mol Pubchem ID :11776298
Synonyms :

Safety of [ 153034-80-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153034-80-1 ]

  • Upstream synthesis route of [ 153034-80-1 ]
  • Downstream synthetic route of [ 153034-80-1 ]

[ 153034-80-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 113975-22-7 ]
  • [ 74-88-4 ]
  • [ 153034-80-1 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78℃; for 0.5 h; Inert atmosphere
2-Fluoro-4-iodo-3-methylpyridine (0412) To a solution of LDA (68 mL, 135 mmol) at −78° C. was added a solution of 2-fluoro-3-iodopyridine (30 g, 135 mmol) in THF (100 mL), and the mixture is stirred for 1 hour at −78° C. under nitrogen. MeI (25 mL, 405 mmol) was then added, and the mixture was stirred for 30 min at −78° C. The mixture was quenched with sat. aq. NaHCO3 solution at −78° C. and then extracted with ether. The combined ether extracts were dried with MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=4:1) to give the title compound as a brown solid (22 g, 69percent). (0413) MS (ES+) C6H5FIN requires: 237, found: 238 [M+H]+.
72% With n-butyllithium; diisopropylamine In tetrahydrofuran EXAMPLE 4
2-Fluoro-4-iodo-3-methylpyridine (6)
To a solution of LDA, freshly prepared from diisopropylamine (0.126 mL, 0.899 mmol) and n-BuLi (0.899 mmol), in THF (2 mL) at -78° C. is cannulated a solution of 2-fluoro-3-iodopyridine (200 mg, 0.897 mmol) in 0.4 mL of THF, and the mixture is stirred for 1 hour at -78° C. under nitrogen.
Iodomethane (0.17 mL, 2.73 mmol) is added neat and the mixture is stirred for 30 min. at -78° C.
The mixture is quenched with saturated sodium bicarbonate solution at -78° C. and then extracted with ether.
Combined ether extracts are dried (MgSO4) and concentrated in vacuo.
The residue is purified by radial plc (silica gel, hexanes) to give 154 mg (72percent) of product as an off-white solid having amp of 90-91 ° C.
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[2] Tetrahedron, 2004, vol. 60, # 29, p. 6113 - 6120
[3] Tetrahedron Letters, 1995, vol. 36, # 44, p. 7995 - 7998
[4] Patent: US2017/342078, 2017, A1, . Location in patent: Paragraph 0412; 0413
[5] Patent: US5496952, 1996, A,
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  • [ 153034-80-1 ]
Reference: [1] Patent: WO2016/89722, 2016, A1, . Location in patent: Page/Page column 35
[2] Patent: WO2016/95204, 2016, A1, . Location in patent: Page/Page column 60; 61
  • 3
  • [ 22282-70-8 ]
  • [ 74-88-4 ]
  • [ 153034-80-1 ]
YieldReaction ConditionsOperation in experiment
17.2 g
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78℃; for 2 h; Inert atmosphere
n-Butyl lithium (1.6M hexane solution, 53.8 mL) was added to a solution of diisopropylamine (8.71 g) in THF (200 mL) at -10 C.
After being stirred at the same temperature under nitrogen atmosphere for 1 hour, a solution of 2-fluoro-3-iodopyridine (18.3 g) in THF (70 mL) was added to the reaction mixture at -78 C.
The mixture was stirred at the same temperature under nitrogen atmosphere for 1 hour.
A solution of iodomethane (12.8 g) in THF (30 mL) was added to the reaction mixture at -78 C.
The mixture was stirred at the same temperature under nitrogen atmosphere for 2 hours.
The mixture was quenched with aqueous saturated ammonium chloride solution at 0 C and extracted with ethyl acetate.
The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo.
The residue was passed through NH-silica and concentrated in vacuo.
The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (17.2 g).
1H NMR (300 MHz, CDCl3) delta 2.39 (3H, d, J=1.5 Hz), 7.57-7.63 (1H, m), 7.65-7.70 (1H, m).
Reference: [1] Patent: US2015/119412, 2015, A1, . Location in patent: Paragraph 0495; 0496
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