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[ CAS No. 1017793-20-2 ] {[proInfo.proName]}

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Chemical Structure| 1017793-20-2
Chemical Structure| 1017793-20-2
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Product Details of [ 1017793-20-2 ]

CAS No. :1017793-20-2 MDL No. :MFCD11040606
Formula : C5H2F2IN Boiling Point : -
Linear Structure Formula :- InChI Key :OBVRKNZQNKGNTQ-UHFFFAOYSA-N
M.W : 240.98 Pubchem ID :53249211
Synonyms :

Calculated chemistry of [ 1017793-20-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.87
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 2.8
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.24
Consensus Log Po/w : 2.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.186 mg/ml ; 0.000772 mol/l
Class : Soluble
Log S (Ali) : -1.94
Solubility : 2.77 mg/ml ; 0.0115 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.54
Solubility : 0.0695 mg/ml ; 0.000288 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 1017793-20-2 ]

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

Application In Synthesis of [ 1017793-20-2 ]

* 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.

  • Upstream synthesis route of [ 1017793-20-2 ]
  • Downstream synthetic route of [ 1017793-20-2 ]

[ 1017793-20-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 84476-99-3 ]
  • [ 1017793-20-2 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - -20℃; for 4.5 h; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
A solution of diisopropylamine (17 mL, 122 mmol) was added to 220 mL of THF and cooled to -20 ° C,Under the protection of nitrogen, n-butyllithium (49 mL, 122.5 mmol) was slowly added and the mixture was stirred at -20 ° C for 0.5 h,After cooling to -78 ° C, 30 mL of tetrahydrofuran solution of 2,5-difluoropyridine (13.3 g, 115 mmol) was slowly added dropwise and stirred at this temperature for 4 h.Weigh iodine (32 g, 126 mmol) was dissolved in 100 mL of THF,At -78 ° C slowly dropwise to the above reaction solution, and the mixture was stirred for 1 hour.After adding water (10 mL) and THF (30 mL), the mixture was allowed to warm to room temperature, saturated sodium thiosulfate was added,The organic phase was separated and the aqueous phase was extracted with EA (3 X100 mL). The organic phases were combined, dried over anhydrous sodium sulfate and filtered through the filtrate. The filtrate was concentrated and purified by silica gel column chromatography (PE: ΕΑ = 50: 1) 13.5 g, yield 48percent).
48%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - -20℃; for 4 h; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Preparation example 2:
Preparation of 2,5-difluoro-4-iodopyridine
Diisopropylamine (17 mL, 122 mmol) was added to tetrahydrofuran (220 mL), and the mixture was cooled to -20 °C.
Under the protection of nitrogen, n-butyl lithium (49 mL, 122.5 mmol) was added slowly.
After the addition, the mixture was stirred at -20 °C for 0.5 h, and cooled to -78 °C. 2,5-difluoropyridine (13.3 g, 115 mmol) in tetrahydrofuran (30 mL) was added slowly and stirred at the temperature for 4 h.
Iodine (32 g, 126 mmol) was dissolved in tetrahydrofuran (100 mL), and was slowly added to said reaction solution at -78°C.
After the addition, the mixture was stirred for 1 h.
After adding water (10 mL) and tetrahydrofuran (30 mL), the temperature was increased to room temperature.
Saturated sodium thiosulfite solution was added.
The organic phase was seperated, and the water phase was extracted with acetic ether (3x100 mL).
The organic phases were combined, dried by anhydrous sodium sulfate, filtrated under suction, and the filtrate was concentrated and then subjected to silica gel column chromatography (petroleum ether: acetic ether=50:1) to get the title compound (13.5 g, yield: 48percent).
44%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78℃; for 3 h;
Stage #2: With iodine In tetrahydrofuran; hexanes at -78℃; for 1 h;
n-Butyllithium (2.5 M in hexanes, 18.6 mL, 46.5 mmol) was added to a solution of diisopropylamine (6.51 mL, 46.1 mmol) in anhydrous tetrahydrofuran (85 mL) at -78°C and stirred at this temperature for 1 hour. A solution of 2,5-difluoropyridine (5.0 g, 43 mmol) in anhydrous THF (12 mL) was added dropwise via cannula and the reaction was stirred at -78°C for 3 hours. After this time, iodine (12.1 g, 47.8 mmol) intetrahydrofuran (50 mL) was added dropwise via cannula to the reaction at -78°C and stirred at this temperature for 1 hour after complete addition. Water (100 mL) was added to the reaction and the temperature was allowed to come to RT. The reaction was extracted with diethyl ether (3x100 mL). The combined organics were washed with brine (100 mL), dried (MgS04), filtered and concentrated. The crude was purified via flash chromatography using an Analogix SF40-80g column and an eluant of ethyl acetate in heptane (0-10percent) to afford the title compound as a yellow solid (4.60 g, 44percent). LC-MS m/z 242.0 (M+1 ). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.39 (t, J=3.71 Hz, 1 H) 7.96 (d, J=1.56 Hz, 1 H).
Reference: [1] Patent: CN104910137, 2017, B, . Location in patent: Paragraph 0213-0216
[2] Patent: EP3091008, 2016, A1, . Location in patent: Paragraph 0167; 0168
[3] Patent: WO2011/73845, 2011, A1, . Location in patent: Page/Page column 116-117
  • 2
  • [ 108-18-9 ]
  • [ 84476-99-3 ]
  • [ 1017793-20-2 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.666667 h;
Stage #2: at -78℃; for 4.5 h;
Stage #3: With iodine In tetrahydrofuran; hexane at -78℃; for 1 h;
n-BuLi 2.5M in hexanes (4.9 ml_, 12.25 mmol) was added to a solution of diisopropylamine (1.7 ml_, 12.20 mmol) in tetrahydrofuran (22 ml.) at -2O0C1 under nitrogen atmosphere, over a period of 10 minutes. The solution was stirred at -2O0C for 30 min and then it was cooled to -780C. A solution of 2,5-difluoropyridine (1.33 g, 11.5 mmol) in tetrahydrofuran (3 mL) was added over a period of 30 min and the mixture was stirred at -780C for 4 hours. After this time, a solution of iodine (3.20 g, 12.6 mmol) in tetrahydrofuran (10 mL) was added dropwise and the mixture was stirred at -780C for 1 hour. Water (1 mL) and tetrahydrofuran (3 mL) were added and the temperature was allowed to raise until room temperature, then water (25 mL) and aqueous sodium bisulphite 40percent p/v (3 mL) were added. The organic layer was separated and the aqueous layer was extracted with diethyl ether (3x50 mL), the combined organic layers were washed with brine, dried over anhydrous magnesium sulphate and the solvent removed under reduced pressure. The residue was purified by silica flash chromatography (5percent diethyl ether in hexanes) to yield the title compound (1.35 g, 48percent) as a white crystalline solid.
Reference: [1] Patent: WO2008/107125, 2008, A1, . Location in patent: Page/Page column 43-44
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