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[ CAS No. 1211580-54-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1211580-54-9
Chemical Structure| 1211580-54-9
Chemical Structure| 1211580-54-9
Structure of 1211580-54-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1211580-54-9 ]

CAS No. :1211580-54-9 MDL No. :MFCD18257229
Formula : C6H4BrF2N Boiling Point : -
Linear Structure Formula :- InChI Key :MNMLGZMORMDPJI-UHFFFAOYSA-N
M.W : 208.00 Pubchem ID :58579539
Synonyms :

Calculated chemistry of [ 1211580-54-9 ]      Expand+

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) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 2.9
Consensus Log Po/w : 2.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.266 mg/ml ; 0.00128 mol/l
Class : Soluble
Log S (Ali) : -2.1
Solubility : 1.63 mg/ml ; 0.00786 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 : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 1211580-54-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:1759
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1211580-54-9 ]

* 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 [ 1211580-54-9 ]
  • Downstream synthetic route of [ 1211580-54-9 ]

[ 1211580-54-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 131747-63-2 ]
  • [ 1211580-54-9 ]
YieldReaction ConditionsOperation in experiment
54% at 20℃; for 16 h; [0207] Step 1: 4-Bromo-2-(difluoromethyl)pyridine : To a 4- bromopicolinaldehyde (5.0 g, 26.88 mmol) was added diethylaminosulfur trifluoride (7.03 mL, 53.7 mmol), and the mixture was stirred at rt for 16 h. The reaction was quenched with aq. sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3 X 100 mL). The combined organic layers were washed with brine (2 X 50 mL), dried over sodium sulfate, filtered, concentrated and purified by column chromatography (100- 200 silica) using 5percent ethyl acetate in hexane as eluent to afford 4-bromo-2- (difluoromethyl)pyridine (3.0 g, 14.492 mmol, 54percent yield ). lH NMR (400 MHz, CDC13) δ = 8.48 (d, J = 4.9 Hz, 1H), 7.82 (d, J = 1.5 Hz, 1H), 7.66-7.50 (m, 1H), 6.60 (t, 1H). LCMS: 207.9 [M+H]+.
49.7% With diethylamino-sulfur trifluoride In chloroform at 0 - 20℃; for 12 h; DAST (0.620 mL, 4.69 mmol) was added dropwise to a solution of 4-bromopicolinaldehyde (700 mg, 3.76 mmol) in Chloroform (21 mL) at 0° C. The reaction mixture was stirred at 20° C. for 12 h. The reaction mixture was poured in to saturated NaHCO3 solution (20 mL), and was extracted with DCM (2×20 mL). The DCM layer was dried over anhydrous Na2SO4, filtered and filtrate was evaporated to afford 4-bromo-2-(difluoromethyl)pyridine (400 mg, 1.870 mmol, 49.7percent yield) as light yellow solid, LCMS (m/z) 208.0 [M+H]+.
49.7% With N,N-diethyltrifluoromethanesulfenamide In chloroform at 0 - 20℃; for 12 h; DAST (0.620 mL, 4.69 mmol) was added dropwise to a solution of 4- bromopicolinaldehyde (700 mg, 3.76 mmol) in Chloroform (21 mL) at 0 °C. The reaction mixture was stirred at 20 °C for 12h. The reaction mixture was poured in to saturated NaHC03 solution (20 mL), and was extracted with DCM (IX 20 mL). The DCM layer was dried over anhydrous Na2S04, filtered and filtrate was evaporated to afford 4-bromo- 2-(difluoromethyl)pyridine (400 mg, 1.870 mmol, 49.7 percent yield) as light yellow solid, LCMS (m/z) 208.0 [M+H]+.
32% With diethylamino-sulfur trifluoride In chloroform at 0 - 20℃; Inert atmosphere Example 30i
4-Bromo-2-(difluoromethyl)pyridine
Diethylaminosulphur trifluoride (4.08 mL, 33.31 mmol) was added to 4-bromopicolinaldehyde (0.267 M in chloroform) (100 mL, 26.7 mmol) at 0° C. under an atmosphere of argon.
The reaction mixture was stirred over night while the temperature was raised to room temperature.
The reaction was quenched by addition of aqueous sodium bicarbonate (sat.) and was further diluted with dichloromethane.
The solids were filtered off through a pad of Celite.(R)..
The organic layer was collected and the water phase was extracted with dichloromethane (*3).
The organic layers were pooled, dried (Na2SO4), filtered and concentrated.
Purification by silica chromatography using 0 to 60percent diethyl ether in pentane gave the title compound (1.78 g, 32percent).
1H NMR (400 MHz, DMSO-d6) δ ppm 8.59 (d, 1H) 7.98 (d, 1H) 7.90 (dt, 1H) 6.98 (t, 1 H); MS (APCI+) m/z 208, 210 [M+H]+.
800 mg With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; Inert atmosphere Description 1284-Bromo-2-(difluoromethyl)pyridine (D128)To a solution of 4-bromopicolinaldehyde (1 g) in DCM (20 mL) stirred under nitrogen atmosphere at 0°C was added DAST (1.065 mL). The reaction mixture was stirred at RT overnight. To the mixture was added water, and then extracted with DCM (3 x50 mL). The organic phase was washed with saturated NaHCO3, water, and brine, then dried over MgSO4 and filtered to give the titlecompound (800 mg) as yellow oil. MS (ESI): C6H4BrF2N requires 207; found no mass.

Reference: [1] Patent: WO2016/161160, 2016, A1, . Location in patent: Paragraph 0207
[2] Patent: US2015/152108, 2015, A1, . Location in patent: Paragraph 0480; 0481
[3] Patent: WO2016/79709, 2016, A1, . Location in patent: Page/Page column 179
[4] Patent: US2010/125082, 2010, A1, . Location in patent: Page/Page column 24; 25
[5] Patent: WO2015/180612, 2015, A1, . Location in patent: Page/Page column 78
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