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[ CAS No. 872365-91-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 872365-91-8
Chemical Structure| 872365-91-8
Chemical Structure| 872365-91-8
Structure of 872365-91-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 872365-91-8 ]

CAS No. :872365-91-8 MDL No. :MFCD16140194
Formula : C6H4BrF2N Boiling Point : -
Linear Structure Formula :- InChI Key :ZTBGDNNRDRISQZ-UHFFFAOYSA-N
M.W :208.00 Pubchem ID :10104489
Synonyms :

Calculated chemistry of [ 872365-91-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.0
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) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 2.9
Consensus Log Po/w : 2.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.165 mg/ml ; 0.000792 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.743 mg/ml ; 0.00357 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.49
Solubility : 0.0673 mg/ml ; 0.000324 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 872365-91-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310+P330-P302+P352-P305+P351+P338 UN#:2810
Hazard Statements:H301-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 872365-91-8 ]

* 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 [ 872365-91-8 ]
  • Downstream synthetic route of [ 872365-91-8 ]

[ 872365-91-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 34160-40-2 ]
  • [ 872365-91-8 ]
YieldReaction ConditionsOperation in experiment
89% With diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 18 h; Step 3. Preparation of 2-bromo-6-(difluoromethyl)pyridine To a solution of 6-bromopicolinaldehyde (2.10 g, 11.29 mmol) in dichloromethane (20 mL) was added diethylaminosulfur trifluoride (1.94 mL, 14.68 mmol) at 0 °C. The reaction mixture was allowed to warm to ambient temperature and stirred for 18 h, and then poured into an ice cold solution of saturated sodium bicarbonate (300 mL). The mixture was extracted with ethyl acetate (2 χ 120 mL). The combined organic phase was washed with saturated sodium bicarbonate (80 mL), brine (2 χ 50 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo afforded the title compound as a brown oil (2.17 g, 89percent yield): H NMR (300 MHz, CDCI3) δ 7.75-7.70 (m, 1 H), 7.65-7.60 (m, 2H), 6.60 (t, J = 55.1 Hz, 1 H).
80% With diethylamino-sulfur trifluoride In dichloromethane at 0 - 25℃; for 12 h; Inert atmosphere DAST (17.76 mL, 134.40 mmol) was added dropwise to 6-bromopicolinaldehyde (10 g, 53.76 mmol) in DCM (150 mL) cooled to 0 °C over a period of 10 minutes. The resulting mixture was stirred at 25 °C for 12 hours. The reaction mixture was quenched with water (20 mL) and basified by the addition of NaHC03 (sat. aq.). The aqueous phase was extracted with DCM (3 x 150 mL), the organic layer was dried over Na2S04, filtered and evaporated to afford a brown liquid. The crude product was purified by flash silica chromatography, elution gradient 0 to 8percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 2-bromo-6-(difluoromethyl)pyridine (Intermediate 43; 9.00 g, 80percent) as a colourless liquid. H NMR (400 MHz, CDCb, 22 °C) δ 6.59 (IH, t), 7.58 - 7.65 (2H, m), 7.71 (IH, t). m/z (ES+), [M+H]+ = 208/210.
68% With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; Preparation 29
Synthesis of 2-bromo-6-difluoromethyl-pyridine
Add diethylaminosulfur trifluoride (31.5 mL, 0.238 mol) dropwise over 20 min to a stirring cooled solution of 6-bromo-pyridine-2-carbaldehyde (30.40 g, 0. 158 mol) in dichloromethane (600 mL) at 0° C. and warm to room temperature overnight.
Divide the reaction mixture in two batches of equal volume for ease of working up.
Slowly add, using extreme caution, a saturated aqueous solution of sodium bicarbonate over 30 min.
Wash the aqueous layer once with dichloromethane.
Dry the combined organic layers over sodium sulfate, filter, and concentrate.
Purify resulting crude material by silica gel chromatography, gradient eluding from 1:99 to 10:90 using ethyl acetate:iso-hexane, to give the title compound (22.60 g, 68percent) and a second fraction (9.4 g, 90percent wt/wt purity, 26percent) which are used with our further purification. 1H NMR (CDCl3) δ 6.59 (t, 1H), 7.61 (m, 2H), 7.73(t, 1H).
1.87 g With diethylamino-sulfur trifluoride In dichloromethane for 2 h; Cooling with ice Step 1: Synthesis of 2-bromo-6-(difluoromethyl)pyridine (0396) 3.81 g (23.6 mmol) of (diethylamino)sulfur trifluoride were added with ice cooling to a mixed solution of 2.00 g (10.8 mmol) of 6-bromopicolinaldehyde and 40 ml methylene chloride. After completion of the addition, said reaction mixture liquid was stirred for 2 hours with ice cooling. After completion of the stirring, the reaction was stopped by addition of 30 ml of saturated aqueous sodium hydrogen carbonate solution, and said reaction liquid was extracted with methylene chloride (2×30 ml). The organic layer obtained was washed with water, then dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=10:0 to 8:2), and 1.87 g of the desired compound were obtained as a white solid. (0397) 1H-NMR (CDCl3, Me4Si, 300 MHz): δ 7.73-7.58 (m, 3H), 6.58 (t, 1H, J=56 Hz).

Reference: [1] Patent: WO2017/201468, 2017, A1, . Location in patent: Page/Page column 236
[2] Patent: WO2017/80979, 2017, A1, . Location in patent: Page/Page column 124; 125
[3] Patent: US2009/253750, 2009, A1, . Location in patent: Page/Page column 9
[4] Patent: US2016/221998, 2016, A1, . Location in patent: Paragraph 0396; 0397
  • 2
  • [ 872365-91-8 ]
  • [ 1315611-68-7 ]
YieldReaction ConditionsOperation in experiment
770 mg With copper(I) oxide; ammonium hydroxide; potassium carbonate; N,N`-dimethylethylenediamine In ethylene glycol for 22 h; Reflux Step 2: Synthesis of (6-difluoromethyl)pyridin-2-amine (0398) 13 ml of aqueous ammonia (28 wt. percent) and 250 mg (1.81 mmol) of potassium carbonate were added at room temperature to a mixed solution of 1.86 g (8.94 mmol) of 2-bromo-6-(fluoromethyl)pyridine, 64 mg (0.447 mmol) of copper(1) oxide, 80 mg (0.908 mmol) of N,N′-dimethylethylenediamine and 18 ml ethylene glycol. After completion of the addition, said reaction mixture liquid was stirred for 22 hours with heating under reflux. After completion of the stirring, the reaction was stopped by addition of 30 ml of water, and said reaction liquid was extracted with ethyl acetate (2×20 ml). The organic layer obtained was washed with water, then dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 6:4), and 770 mg of the desired compound were obtained as a colorless liquid. (0399) 1H-NMR (CDCl3, Me4Si, 300 MHz): δ 7.53 (dd, 1H, J=7.2 Hz, 8.1 Hz), 6.94 (d, 1H, J=7.2 Hz), 6.57 (d, 1H, J=8.1 Hz), 6.42 (t, 1H, J=56 Hz), 4.58 (brs, 2H).
Reference: [1] Patent: US2016/221998, 2016, A1, . Location in patent: Paragraph 0398; 0399
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