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[ CAS No. 175205-81-9 ] {[proInfo.proName]}

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Chemical Structure| 175205-81-9
Chemical Structure| 175205-81-9
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Product Details of [ 175205-81-9 ]

CAS No. :175205-81-9 MDL No. :MFCD00153085
Formula : C6H3BrF3N Boiling Point : -
Linear Structure Formula :- InChI Key :WZVHLUMAQLUNTJ-UHFFFAOYSA-N
M.W : 225.99 Pubchem ID :2781543
Synonyms :

Calculated chemistry of [ 175205-81-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.94
TPSA : 12.89 ?2

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) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.76
Log Po/w (WLOGP) : 4.02
Log Po/w (MLOGP) : 2.33
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 2.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.109 mg/ml ; 0.000481 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.466 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0383 mg/ml ; 0.000169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 175205-81-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 175205-81-9 ]

* 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.

  • Downstream synthetic route of [ 175205-81-9 ]

[ 175205-81-9 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 124-38-9 ]
  • [ 175205-81-9 ]
  • 4-(trifluoromethyl)-2-pyridinecarboxylic acid [ No CAS ]
  • 2
  • [ 81565-18-6 ]
  • [ 175205-81-9 ]
YieldReaction ConditionsOperation in experiment
With trimethylsilyl bromide; In propiononitrile; for 22h;Heating / reflux; A mixture of 2-chloro-4-(trifluoromethyl)pyridine (2.70 g, 14.9 mmol) and bromotrimethylsilane (3.90 mL, 29.6 mmol) in propanenitrile (15.0 mL) was heated under reflux for 22 h. The product (very volatile) was carefully rotary evaporated to give 4.07 g (propanenitrile contained) of thick light brown suspension w/o further purification. LC-MS calculated for C6H3BrF3N (M+H) 226.9; found 225.9/227.8.
  • 3
  • [ 124-38-9 ]
  • [ 175205-81-9 ]
  • 2-bromo-4-(trifluoromethyl)pyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% To Diisopropylamine ( 1 equi) dissolved in THF( 30 mL) added BuLi ( 2.5 M solution in hexane, 9 mL, 1 equi.) and stirred the mixture at room temperature for 30 min. A solution of the bromo pyridine, 1 (5 gm, 1 equi.) in THF (50 mL) was cooled down to -78°C and added the pre- generated LDA to it via a canula. The reaction mixture was continued to stirr at -78°C for further one hour and poured to an excess of crushed dry ice immersed in THF (~ 50 mL). The stirring was continued for 30min allowing the temperature to rise to ice temperature. Evaporated off all the volatiles to obtain 5.8gm (97percent) of 2 which was used for further step without purification.
  • 4
  • [ 832715-89-6 ]
  • [ 175205-81-9 ]
  • [1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-(5'-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 165℃; for 0.333333h;Irradiation; A mixture of [1- (4-METHANESULFONYL-PHENYL)-LH-PYRAZOLO [3, 4-d] pyrimidin-4-yl]-piperidin-4-yl- amine (100 mg, 0. 24 mmol), <strong>[175205-81-9]2-bromo-4-trifluoromethylpyridine</strong> (166 mg, 0. 73 mmol), and potassium carbonate (102 mg, 0. 73 mmol) in DMF (1. 0 mL) was heated under microwave irradiation for 20 minutes at 165 °C. The crude mixture was purified by HPLC to provide compound A128 as a white solid (41 mg, 32 percent). Exact mass calculated for C23H22F3N702S 517. 15, found 518. 2 (MH+).
  • 5
  • [ 73874-95-0 ]
  • [ 175205-81-9 ]
  • [ 898271-32-4 ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine; In dimethyl sulfoxide; at 120℃; for 17h; tert-Butyl {l-[4-(trifluoromethyl)pyridin-2-yl]piperidin"4-yl}carbamate; A solution of <strong>[175205-81-9]2-bromo-4-trifluoromethylpyridine</strong> (1.0Og, 4.42mmol), tert-butyl piperidine-4- ylcarbamate (0.93g, 4.65mmol) and TEA (0.67mL, 4.86mmol) in DMSO (5mL) was heated at 1200C for 17h. The reaction mixture was evaporated to dryness, Et2O was added, and the organic phase was washed with water, brine and evaporated to dryness. The residue was purified using the Biotage Horizon HRFC system eluting with 22percent EtOAc in petroleum ether EPO <DP n="195"/>(40-60°C) to give the title compound (1.08g, 71percent) as a solid. 1H NMR(500MHz, CDCl3): 8.30 (d, IH), 6.82 (s, IH), 6.77 (d, IH), 4.49 (bs, IH), 4.36-4.22 (m, 2H), 3.74 (bs, IH), 3.06 (td, 2H), 2.10-2.04 (m, 2H), 1.56-1.38 (m, 11H); 13C NMR(CDCl3): 159.4, 155.4, 149.5, 140.1, 139.9, 124.5,122.4, 108.1, 102.7, 79.8, 48.3, 44.4, 32.3, 28.6; Mass Spectrum: M+H 5 346.
  • 6
  • 5-ethoxy-3-hydroxy-3-(trifluoromethyl)pent-4-enenitrile [ No CAS ]
  • [ 175205-81-9 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogen bromide; In dichloromethane; at 20℃;Product distribution / selectivity; Dry HBr gas was introduced at room temperature into a solution of 5 g of 5-ethoxy-3-hydroxy-3-(trifluoro-methyl)pent-4-enenitrile in 100 ml of dichloromethane. The conversion was then monitored by HPLC and, once the content of product in the reaction mixture did not increase any further, the mixture was isolated and purified by aqueous workup and distillation. Yield: 3.9 g (73percent).
32% With hydrogen bromide; In acetic acid; at 0 - 5℃; for 1h; 100 g of hydrogen bromide were initially charged in glacial acetic acid (33percent) and cooled to from 0 to 5° C. by external cooling with ice. 10 g of 5-ethoxy-3-hydroxy-3-(trifluoromethyl)pent-4-enenitrile were then slowly added dropwise to this mixture within 1 h. The conversion was then monitored by HPLC and, once the content of product in the reaction mixture did not increase any further, the mixture was isolated and purified by aqueous workup, extraction and distillation as in the previous examples. 3.5 g (32percent) of product were thus obtained, whose structure was confirmed with the aid of the mass spectrum and by comparison with the spectroscopic data of the analogous chlorine compound.
  • 7
  • [ 193065-68-8 ]
  • [ 175205-81-9 ]
  • [ 917760-98-6 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 20℃; for 19h; Preparation 11a: 3-(4-trifluoromethylpyridin-2-yl)propionic acid ethyl ester; A solution of 3-ethoxy-3-oxopropylzinc bromide in tetrahydrofuran (0.5 M, 67 mL) was added dropwise over a period of 1 hour to a mixture of <strong>[175205-81-9]2-bromo-4-trifluoromethylpyridine</strong> (6.9 g), tetrakis(triphenylphosphine)palladium(0), (0.60 g) and tetrahydrofuran (20 mL) at room temperature. The resulting mixture was stirred at room temperature for 18 hours, diluted with water (150 mL) and extracted with methyl tert-butyl ether. The combined extracts were dried over magnesium sulphate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of pentane, dichloromethane and ethyl acetate (1:1:0, 0:1:0 and 0:5:1 by volume), gave title compound as a yellow oil, 4.2 g.1H NMR (CDCl3): delta 1.25 (t, J=7.0 Hz, 3H), 2.85 (t, J=7.3 Hz, 2H), 3.20 (t, J=7.3 Hz, 2H), 4.10 (q, J=7.0 Hz, 2H), 7.35 (d, J=4.7 Hz, 1H), 7.40 (s, 1H), 8.70 (d, J=4.7 Hz, 1H).MS: ESI (+ve) (Method B): 248 (M+H)+, Retention time 3.33 min.
  • 8
  • [ 206446-38-0 ]
  • [ 175205-81-9 ]
  • [ 1161829-68-0 ]
YieldReaction ConditionsOperation in experiment
37% With iodobenzene;tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In tetrahydrofuran; at 20 - 65℃; for 2.16667h; In a separate flask, Pd2(dba)3 (45 mg, 0.05 mmol), P(2-furyl)3 (46 mg, 0.2 mmol) and <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (1.36 mg, 6 mmol) were mixed in THF (1 mL) under N2 for 10 min. This mixture was added to the organozinc reagent solution mentioned above, followed by iodobenzene (1.36 g, 6 mmol) in THF (10 mL). The mixture was heated at 65 °C for 2 h, then cooled, diluted with ethyl acetate and filtered over celite. The filtrate was washed with NaHCO3 (x2), brine (xl) and concentrated. The crude was purified by column chromatography to give the desired product tert-butyl 3-(4-(trifluoromethyl)pyridin-2- yl)azetidine-l-carboxylate (554 mg, 37percent yield): 1H NMR (400 MHz, CDCl3): delta 8.15(d, IH), 7.42 (s, IH), 7.42(d, IH), 4.34 (t, 2H), 4.19 (dd, 2H), 3.95 (dq, IH) 1.47 (s, 9H); MS (ESI) m/z: Calculated for C14HnF3N2O2: 302.29; found: 247.0 (M-1Bu)+.
  • 9
  • [ 76003-29-7 ]
  • [ 175205-81-9 ]
  • [ 1154868-68-4 ]
YieldReaction ConditionsOperation in experiment
92% Step 1: ferf-Butyl 3-oxo-4-r4-(trifluoromethyl)pyridin-2-yllpiperazine-l-carboxylate (II)A mixture of l-Boc-3-oxopiperazine (1.0 eq.), <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (1.5 eq.) and Cs2CO3 (1.5 eq.) in 1,4-dioxane (0.5M) was degassed under Argon flow for 30 min, then Pd(OAc)2 (0.1 eq.) and Xantphos (0.15 eq.) were added, the vial was sealed and stirring was continued at 1100C for 18 hr. Reaction mixture was diluted with EtOAc and filtered through a pad of SolcaFloc.(R). 200 FCC. After removal of the solvent, the crude product was purified by flash column chromatography on silica gel using 10- 40percent EtO Ac/Petroleum ether as eluent to afford the desired product Il as yellow solid (92percent yield). 1R NMR (400 MHz, CDCl3, 300K) delta 8.57 (IH, d, J = 4.8 Hz), 8.40 (IH, bs), 7.32 (IH, d, J = 4.8 Hz), 4.31 (2H, s), 4.17 (2H, t, J = 5.3 Hz), 3.76 (2H, t, J = 5.3 Hz), 1.50 (9H, s). MS (ES) Ci5Hi8F3N3 O3 requires: 345, found: 346 (M+H)+.
  • 11
  • [ 191171-55-8 ]
  • [ 175205-81-9 ]
  • [ 1220100-83-3 ]
  • 12
  • [ 5419-55-6 ]
  • [ 175205-81-9 ]
  • C15H24BF3NO3(1-)*Li(1+) [ No CAS ]
  • 13
  • [ 175205-81-9 ]
  • [ 142946-79-0 ]
YieldReaction ConditionsOperation in experiment
56% With palladium diacetate; potassium carbonate; at 120℃; for 48h;Inert atmosphere; General procedure: 2-Iodopyrazine (5.00 g, 24.3 mmol), PdII(OAc)2 (34 mg, 0.151 mmol), K2CO3 (3.4 g, 24.6 mmol) and poly(ethylene glycol) (Mw 4000, 24.0 g) were combined in an argon-purged flask. The mixture was gradually heated to 120 C and the temperature maintained for 48 h with stirring. The mixture was cooled to ca. 80 C and warm water (30 mL) was added to prevent solidification. On cooling to room temperature, further water (100 mL) was added and the suspension exhaustively extracted with ethyl acetate. The combined extracts were washed once with saturated aqueous Na2S2O3 and then thrice with brine. The organic layer was dried over MgSO4 and solvent removed under vacuum. The residue was triturated with n-pentane and the white crystalline solid filtered off, washed with n-pentane and dried. Yield: 1.35 g (70%).
52% 2.2 Synthesis of 4,4'-bis(trifluoromethyl)-2,2'-bipyridine 2-Bromo-4-trifluoromethyl pyridine (1.2 g, 5.31 mmol) was placed in a round bottom flask with 7.14 g of activated copper bronze. The reaction flask was then flushed with N2 and a reflux condenser was affixed. The reaction was then heated to 190 C for 16 h. The reaction was then cooled to room temperature and the ligand extracted with acetone and chloroform (?100 mL). The organic fraction was then extracted with 1.2 N HCl. Once the aq. fraction turned blue, the organic fraction was extracted then evaporated to afford a yellow oil. The ligand was then purified by vacuum sublimation (52% yield). Spectroscopic data matched literature values [12] .
  • 14
  • [ 149793-69-1 ]
  • [ 6921-34-2 ]
  • [ 175205-81-9 ]
  • [ 939426-21-8 ]
YieldReaction ConditionsOperation in experiment
66.6% To an oven-dried round bottomed flask was added nBuLi (2.5 M in hexanes, 0.95 ml, 2.38 mmol, 1.17 eq) at -60° C. under N2. An Et2O solution (5 mL) of <strong>[175205-81-9]2-bromo-4-trifluoromethylpyridine</strong> (448 mg, 2.0 mmol) was added dropwise at -60 to -55° C. The resulting solution was stirred at the above temperate for 30 min. The mixture was cooled to -78° C., an Et2O solution (2 mL) of 3-fluoro-5-trifluoromethyl-benzonitrile (390 g, 2.06 mmol) was added dropwise. The resulting solution was stirred -78 to -70° C. for 1.5 h. Pretreated TMSCl (0.26 ml) was added dropwise at -78° C. The mixture was stirred at -78° C. for 15 min, and then warmed up to r.t. for 45 min. It was cooled back to -78° C., and benzyl magnesium chloride (1.0 ml, 2.0 mmol) was added dropwise. The resulting mixture was stirred at -78° C. for 1 h, and then at r.t. for 0.5 h. It was quenched by adding sat'd NH4Cl and 1N HCl, and stirred for 10 min. It was extracted with EtOAc, washed with 1N NaOH, sat'd NaHCO3, H2O, brine, dried (MgSO4), filtered, and concentrated to dryness. The residue was purified by flash chromatography (silica gel, hexanes/EtOAc) to give 1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenyl-1-(4-(trifluoromethyl)pyridin-2-yl)ethanamine as light brownish gum (0.57 g, yield: 66.6percent). LC-MS ESI (10-90percent MeOH in H2O with 0.1percent TFA in a 4-min run), retention time=3.32 min, 429.13 (M+H).
  • 15
  • [ 813-19-4 ]
  • [ 175205-81-9 ]
  • [ 1334675-40-9 ]
YieldReaction ConditionsOperation in experiment
36% trans-bis(triphenylphosphine)palladium dichloride; In 1,4-dioxane; at 140℃; for 3h;Microwave irradiation; Inert atmosphere; Sealed; Step 1In a microwave vial <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (330 mg, 1.46 mmol), bis(tributylyln) (1.44 mL, 2.85 mmol), and PdCl2(PPh3)2 (51 mg, 0.073 mmol) were suspended in 1,4-dioxane (15 mL).The mixture was degassed with a gentle stream of N2 for 15 min then the vial was then sealed and heated in a microwave reactor at 140° C. for 3 h.The reaction mixture was cooled to room temperature and concentrated.The residue was purified by SiO2 chromatography (5-20percent EtOAc/hexane) to give 229 mg (36percent) of 2-tributylstannanyl-4-trifluoromethyl-pyridine.
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; ;