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[ CAS No. 1000773-62-5 ] {[proInfo.proName]}

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Chemical Structure| 1000773-62-5
Chemical Structure| 1000773-62-5
Structure of 1000773-62-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1000773-62-5 ]

CAS No. :1000773-62-5 MDL No. :MFCD11846578
Formula : C7H5BrF3N Boiling Point : -
Linear Structure Formula :- InChI Key :UMXIAVUQROUXKO-UHFFFAOYSA-N
M.W : 240.02 Pubchem ID :21441094
Synonyms :

Calculated chemistry of [ 1000773-62-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.08
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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.33
Log Po/w (WLOGP) : 4.0
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 3.35
Consensus Log Po/w : 2.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.222 mg/ml ; 0.000925 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 1.38 mg/ml ; 0.00576 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.016 mg/ml ; 0.0000668 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 1000773-62-5 ]

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#:1760
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1000773-62-5 ]

* 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 [ 1000773-62-5 ]

[ 1000773-62-5 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 31181-84-7 ]
  • [ 1000773-62-5 ]
YieldReaction ConditionsOperation in experiment
86% With phosphorus tribromide; In dichloromethane; at 0 - 20℃; To an ice-cooled solution of (5-trifluoromethyl-pyridin-2-yl)-methanol (300 mg, 1.69 mmol) inDCM (10 mL) is added phosphoros tribromide (96 mul_, 1.02 mmol) and the reaction mixture is stirred for 2 h at room temperature. The reaction mixture is quenched with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated under reduced pressure.Yield: 350 mg (86% of theory); ESI Mass spectrum: [M+H]+ = 239Retention time HPLC: 1.37 min (method J).
77% With 1H-imidazole; bromine; triphenylphosphine; In dichloromethane; for 3h; 2-(bromomethyl)-5-(trifluoromethyl)pyridine<strong>[31181-84-7][5-(trifluoromethyl)pyridin-2-yl]methanol</strong> (2.Og, 11.29 mmol) was dissolved in DCM (20 ml_) at r.t. Imidazole (824 mg, 11.9 mmol) was added and allowed to dissolve. Triphenylphosphine (3.36 g, 12.4 mmol) was then added and dissolved. Bromine (0.58 ml_, 11.3 mmol) was added last and stirred for 3 hours. The reaction was quenched water and extracted with dichloromethane (2x 25 ml_). The organics were dried with magnesium sulfate and concentrated. The crude product was purified by flash chromatography (heptanes:ethyl acetate) to give the title compound as a clear liquid (2.1 g, 8.75 mmol, 77%).
Reference Production Example 2. In 70 mL of tetrahydrofuran, 4.44 g of (5- trifluoromethylpyridin-2-yl) methanol was dissolved and 1.9 mL of methanesulfonyl chloride and 3.5 mL of triethylamine were added dropwise at 00C. After stirring at the same temperature for 0.5 hours, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was dissolved in 30 mL of N, N-dimethylformamide. To the solution was added 4.4 g of lithium bromide at room temperature. The reaction mixture was heated to 90C and, after stirring for 10 minutes and returning to room temperature, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was subjected to column chromatography to obtain 1.68 g of 2- bromomethyl-5-trifluoromethylpyridine.1H-NMR (CDCl3, TMS) : delta (ppm) 8.84 (IH, s), 7.94 (IH, dd) ,7.59 (IH, d) , 4,59 (2H, s).
With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 3h; Step (ii): 2-(Bromomethyl)-5-(trifluoromethyl)pyridine To a solution of <strong>[31181-84-7][5-(trifluoromethyl)pyridin-2-yl]methanol</strong> (5.0 g, 28.24 mmol) in DCM (50 ml) was added tribromophosphane (0.58 g, 3.50 mmol) at 0 C. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction was then poured into water (50 ml) and the organics were extracted with DCM (2×50 ml), washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound which was used without further purification. MS ES+: 240, 242
With phosphorus tribromide; In dichloromethane; at 20℃; for 3h; Intermediate 1 (390.0 mg, 2.2 mmol) was dissolved in DCM (10 mL). 0 C, a solution of PBr3 (387.0 mg, 1.43 mmol) in DCM (2 mL) was added dropwise. The reaction was carried out for 3 hours at room temperature. TLC showed the reaction was completed. The pH was adjusted to 6-7 with saturated NaHCO3 solution, H2O (15 mL) added and DCM extracted (15 mLx3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (450.0 mg, 80.0% purity, 68.1% yield).

  • 2
  • [ 1000773-62-5 ]
  • [ 102687-64-9 ]
  • [ 1122705-27-4 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol at 20℃; for 0.166667h; 7 Production Example 7. In 20 mL of methanol, 500 mg of 2-bromomethyl-5- trifluoromethylpyridine and 488 mg of S- (3,3,3- trifluoropropyl) benzenethioate were dissolved and 0.4 mL of sodium methoxide (28% methanol solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 10 minutes, 10% hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was subjected to column chromatography to obtain 400 mg of 5-trifluoromethyl-2- (3,3, 3-trifluoropropylsulfanylmethyl) pyridine (hereinafter referred to as the present compound (7)) . The present compound (7) 1H-NMR (CDCl3, TMS) : δ (ppm) 8.80 (IH, s) , 7.92 (IH, dd) , 7.50 (IH, d) , 3.91 (2H, s), 2.65-2.69 (2H, m) , 2,34-2.46 (2H, m).
  • 3
  • [ 1000773-62-5 ]
  • [ 1173155-44-6 ]
  • [ 1173156-00-7 ]
YieldReaction ConditionsOperation in experiment
29% With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 72h; 76.a 2-(Bromomethyl)-5-(trifluoromethyl)pyridine (140 mg, 0.58 mmol), tert-hvXy 7- (4-hydroxy-2-oxopyridin4(2H)-yl)-5-methyl-3,4-dihydro-l/f-pyrido[4,3-δ]indole-2(5H)- carboxylate (230 mg, 0.58 mmol) and K2CO3 (160 mg, 1.16 mmol) were stirred in acetonitrile/DMF (3 mL/0.5mL) for 72 h. The mixture was diluted with methylene chloride, washed with water and concentrated to provide the title compound (96 mg, 29%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.88 (s, IH), 8.00 (dd, J= 8.2, 2.0 Hz, IH), 7.63 (d, J= 8.2 Hz, IH), 7.51 (d, J= 8.2 Hz, IH), 7.36 (d, J= 7.6 Hz, IH), 7.28-7.26 (m, IH), 7.00 (d, J= 7.7 Hz, IH), 6.12 (dd, J= 7.6, 2.7 Hz, IH), 6.04 (d, J= 2.7 Hz, IH), 5.26 (s, 2H), 4.63-4.58 (br m, 2H), 3.87-3.76 (br m, 2H), 3.63 (s, 3H), 2.86-2.76 (br m, 2H), 1.50 (s, 9H).
  • 4
  • [ 1000773-62-5 ]
  • [ 1227472-59-4 ]
  • [ 1227473-73-5 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: tert-butyl (3R)-3-(4-hydroxyphenyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate With potassium carbonate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 2-(bromomethyl)-5-(trifluoromethyl)pyridine In tetrahydrofuran at 70℃; for 6h; 94 tert-butyl (3R)-3-(4-([5-(trifluoromethyl)pyridin-2-yllmethoxy)phenyl)-1-oxa-8-azaspiro[4.5ldecane-8- carboxylate tert-butyl (3R)-3-(4-hydroxyphenyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (500 mg, 1.43 mmol) was dissolved in THF (5 ml_) and potassium carbonate (257 mg, 1.86 mmol) added. The reaction was stirred at r.t. for 15 minutes and then 2-(bromomethyl)-5-(trifluoromethyl)pyridine (515 mg, 2.15 mmol) added. The reaction was heated at 70 C for 6 hours at which time it was cooled to r.t. quenched with water and the aqueous phase extracted with ethyl acetate (2x 10 ml_). The organics were dried with magnesium sulfate and concentrated. The crude product was purified by flash chromatography (ethyl acetate heptanes) to give the title compound as a clear oil (590 mg, 1.19 mmol 84%).
  • 5
  • [ 100366-75-4 ]
  • [ 1000773-62-5 ]
  • 6
  • [ 1000773-62-5 ]
  • tert-butyl N-[(2E)-2-[5-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: toluene / 17 h / Reflux 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 20 °C / Reflux
  • 7
  • [ 1000773-62-5 ]
  • tert-butyl N-(2-[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: toluene / 17 h / Reflux 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 20 °C / Reflux 3.1: palladium 10% on activated carbon; hydrogen; sodium hydroxide / methanol / 2 h
  • 8
  • [ 1000773-62-5 ]
  • [ 122-52-1 ]
  • diethyl [5-(trifluoromethyl)pyridin-2-yl]methyl}phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene for 17h; Reflux; iii Step (iii): Diethyl [5-(trifluoromethyl)pyridin-2-yl]methyl}phosphonate Step (iii): Diethyl [5-(trifluoromethyl)pyridin-2-yl]methyl}phosphonate To a solution of 2-(bromomethyl)-5-(trifluoromethyl)pyridine (3.0 g, 12.5 mmol) in toluene (100 ml) was added triethyl phosphite (6.2 g, 37.0 mmol). The reaction was refluxed for 17 hours and was then concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-50% ethyl acetate n-hexane) to afford the title compound. 1H NMR (400 MHz, DMSO) δ ppm 1.06-1.27 (m, 6H), 3.57-3.65 (m, 2H), 3.95-4.08 (m, 4H), 7.61-7.59 (m, 1H), 8.20-8.18 (m, 1H), 8.90-8.89 (m, 1H) MS ES+: 298
  • 9
  • [ 1000773-62-5 ]
  • 1,3-dimethyl-5-(cyclohexyloxy)pyrazole-4-carbaldehyde oxime [ No CAS ]
  • 1,3-dimethyl-5-(cyclohexyloxy)pyrazole-4-carbaldehyde O-(5-trifluoromethyl-2-pyridyl)methyl oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
321 mg With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 1 To 300 mg (1.23 mmol) of 1,3-dimethyl-5- (cyclohexyloxy) pyrazole-4-carbaldehyde oxime, 5 ml of DMF,804 mg (2.53 mmol) of 2-bromomethyl-5-trifluoromethylpyridine,524 mg (3.80 mmol) of potassium carbonate was added,And the mixture was stirred at room temperature for 16 hours.To the reaction mixture was added 2 M aqueous sodium hydroxide solution,Extraction with ethyl acetate,After drying the organic layer with sodium sulfate,Filtered and concentrated.The obtained residue was subjected to silica gel column chromatography,321 mg of 1,3-dimethyl-5- (cyclohexyloxy) pyrazole-4-carbaldehyde O- (5-trifluoromethyl-2-pyridyl) methyl oxime (compound (1)) was obtained.
  • 10
  • [ 1000773-62-5 ]
  • [ 2973-80-0 ]
  • C14H9BrF3NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
420 mg With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; 5.3 Step 3 Synthesis of intermediate 3 Intermediate 2 (447.8 mg, 1.49 mmol) was dissolved in DMF (6 mL) and 2-bromo-5-hydroxybenzaldehyde (250.0 mg, 1.24 mmol) and K2CO3 (206.3 mg, 1.49 mmol) were added with stirring. Under nitrogen, the reaction was carried out at room temperature for 1.5 hours and TLC showed the reaction was completed. H2O (15 mL) was added and EA extracted (15 mL x 3). The combined organic phases were washed with saturated sodium chloride (15 mL x 3), dried over anhydrous sodium sulfate, filtered, concentrated and purified (SiO2, PE: EA = 40: 1) to give the title compound (420.0 mg, 93.8%).
  • 11
  • [ 124236-37-9 ]
  • [ 1000773-62-5 ]
  • 12
  • [ 1000773-62-5 ]
  • C20H21BF3NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 100 °C / Ionic liquid
  • 13
  • [ 1000773-62-5 ]
  • C14H11BF3NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 100 °C / Ionic liquid 3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.17 h / 0 - 20 °C 3.2: 0.5 h / 20 °C / pH 2 - 3
  • 14
  • [ 1000773-62-5 ]
  • (5RS)-5-(pyrrolidin-1-ylcarbonyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]
  • (5RS)-5-(pyrrolidin-1-ylcarbonyl)-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With caesium carbonate In acetonitrile 23 (5RS)-5-(Pyrrolidin-1-ylcarbonyl)-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (Racemate) Example 23 (5RS)-5-(Pyrrolidin-1-ylcarbonyl)-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (Racemate) (5RS)-5-(Pyrrolidin-1-ylcarbonyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (racemate) (40.0 mg, 169 μmol) was initially charged in acetonitrile (2.0 ml). Caesium carbonate (82.7 mg, 254 μmol) and 2-(bromomethyl)-5-(trifluoromethyl)pyridine (44.7 mg, 186 μmol) were subsequently added. After stirring overnight, the reaction mixture was admixed at room temperature with water, 1 N aqueous hydrochloric acid and ethyl acetate. The organic phase was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. The residue was purified via preparative HPLC (Chromatorex C18, 10 μm, 125 mm*30 mm; eluent: acetonitrile/water gradient). The product-containing fractions were concentrated under reduced pressure, and 44.6 mg (67% of theory) of the title compound were obtained. LC-MS (Method 3): Rt=1.22 min; MS (ESIpos): m/z=396 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) δ[ppm]: -0.149 (0.72), 0.147 (0.71), 1.726 (2.72), 1.738 (3.10), 1.775 (4.76), 1.792 (7.48), 1.809 (5.64), 1.826 (1.77), 1.894 (1.55), 1.911 (4.76), 1.928 (5.91), 1.945 (3.79), 1.962 (1.18), 2.025 (2.84), 2.053 (1.90), 2.328 (0.88), 2.366 (0.64), 2.564 (2.98), 2.574 (2.44), 2.589 (2.03), 2.601 (2.01), 2.613 (3.47), 2.625 (1.98), 2.655 (1.38), 2.669 (1.43), 2.710 (0.77), 3.236 (0.95), 3.253 (1.97), 3.265 (2.17), 3.282 (3.78), 3.329 (2.27), 3.347 (3.67), 3.364 (2.07), 3.377 (2.12), 3.395 (1.00), 3.450 (1.06), 3.467 (2.41), 3.492 (3.06), 3.509 (1.38), 3.599 (1.44), 3.615 (2.87), 3.632 (1.84), 3.640 (2.24), 3.657 (1.00), 4.760 (2.66), 4.775 (3.67), 4.784 (2.76), 5.026 (16.00), 7.383 (4.73), 7.403 (4.96), 8.212 (3.24), 8.233 (3.24), 8.929 (5.73).
  • 15
  • [ 1000773-62-5 ]
  • methyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate [ No CAS ]
  • methyl (5S)-3-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With caesium carbonate In acetonitrile Methyl (5S)-3-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate Methyl (5S)-3-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate Methyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate (187 mg, 947 μmol) was initially charged in acetonitrile (4.0 ml). Caesium carbonate (463 mg, 1.42 mmol) and 2-(bromomethyl)-5-(trifluoromethyl)pyridine (250 mg, 1.04 mmol) were subsequently added. After stirring overnight, the reaction mixture was admixed at room temperature with water, 1 N aqueous hydrochloric acid and ethyl acetate. The organic phase was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. The residue was purified via preparative HPLC (Chromatorex C18, 10 μm, 125 mm*30 mm; eluent: acetonitrile/water gradient). The product-containing fractions were concentrated under reduced pressure, and 185 mg (55% of theory) of the title compound were obtained. LC-MS (Method 3): Rt=1.34 min; MS (ESIpos): m/z=357 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) δ[ppm]: 1.560 (0.40), 1.827 (0.50), 1.841 (0.44), 1.851 (0.42), 2.083 (0.45), 2.092 (0.76), 2.106 (0.76), 2.126 (0.45), 2.135 (0.53), 2.147 (0.47), 2.155 (0.52), 2.163 (0.48), 2.559 (0.44), 2.575 (0.90), 2.589 (0.77), 2.601 (0.78), 2.615 (0.64), 2.637 (0.60), 2.649 (1.13), 2.661 (0.72), 2.691 (0.47), 3.715 (16.00), 4.631 (1.05), 4.641 (1.16), 4.647 (1.36), 4.657 (1.01), 5.063 (5.88), 7.396 (1.64), 7.416 (1.71), 8.223 (1.06), 8.228 (1.09), 8.243 (1.02), 8.249 (1.04), 8.935 (1.74).
  • 19
  • [ 1000773-62-5 ]
  • N-cyclopropyl-3,5-dimethyl-4-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 12 h / 60 °C 2.1: acetic acid; zinc / 15 - 20 °C / Heating 3.1: sodium hydroxide / water; ethanol / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 4.2: 20 °C
  • 20
  • [ 1000773-62-5 ]
  • azetidin-1-yl(3,5-dimethyl-4-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-pyrrol-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 12 h / 60 °C 2.1: acetic acid; zinc / 15 - 20 °C / Heating 3.1: sodium hydroxide / water; ethanol / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 4.2: 20 °C
  • 21
  • [ 1000773-62-5 ]
  • N-cyclobutyl-3,5-dimethyl-4-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 12 h / 60 °C 2.1: acetic acid; zinc / 15 - 20 °C / Heating 3.1: sodium hydroxide / water; ethanol / 80 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 4.2: 20 °C
  • 22
  • [ 1000773-62-5 ]
  • [ 91419-52-2 ]
  • tert-butyl 4-cyano-4-((5-(trifluoromethyl)pyridin-2-yl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: 1-tert-butoxycarbonyl-4-cyanopiperidine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-(bromomethyl)-5-(trifluoromethyl)pyridine In tetrahydrofuran at 20℃; for 16h; 54 Synthesis of A152 To a mixture of tert-butyl 4-cyanopiperidine-1-carboxylate (656 mg, 3.12 mmol) in THF (10 mL) was added dropwise LDA (1.56 mL, 2 M, 3.12 mmol) at -78°C, the mixture was stirred at -78°C for 1 hour, and then 2-(bromomethyl)-5-(trifluoromethyl)pyridine (500 mg, 2.08 mmol) was added. The mixture was warmed to 20°C and stirred for 16 hours. The mixture was poured into water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with brine (2x100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (0~30% of EtOAc in PE) to give tert-butyl 4-cyano-4-((5-(trifluoromethyl)pyridin-2-yl)methyl)piperidine-1- carboxylate (0.3 g, 39%).1H NMR (400 MHz, CDCl3) dH 8.85 (s, 1 H), 7.93 (d, 1 H), 7.50 (d, 1 H), 4.23-4.06 (m, 2 H), 3.15-3.10 (m, 2 H), 3.07-2.97 (m, 2 H), 1.95-1.86 (m, 2 H), 1.68- 1.59 (m, 2 H), 1.4-1.45 (m, 9H).
  • 23
  • [ 1000773-62-5 ]
  • ethyl 8-methyl-4,5-dihydro-1H-furo[2,3-g]indazole-7-carboxylate [ No CAS ]
  • ethyl 8-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-4,5-dihydro-2H-furo[2,3-g]indazole-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% Stage #1: ethyl 8-methyl-4,5-dihydro-1H-furo[2,3-g]indazole-7-carboxylate With sodium hydride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: 2-(bromomethyl)-5-(trifluoromethyl)pyridine In N,N-dimethyl-formamide at 20℃; for 0.75h; 1 Intermediate 8: Step 1 ethyl 8-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-4,5-dihydro-2H-furo[2,3- g]indazole-7-carboxylate In a modification of GP C (conditions B) an ice-cooled solution of ethyl 8-methyl-4,5- dihydro-1H-furo[2,3-g]indazole-7-carboxylate (commercially available; 1.00 eq., 171 mg, 694 μmol) in DMF (6 mL) was treated with sodium hydride (CAS No. [7646-69-7]; 55% purity, 1.2 eq., 36 mg, 830 μmol) for 30 minutes upon which 2-(bromomethyl)-5- (trifluoromethyl)pyridine (1.20 eq., 200 mg, 833 μmol) was added, the reaction mixture warmed to rt and stirring continued for 45 minutes. The reaction mixture was diluted with sat. aqueous ammonium chloride and EtOAc, the phases were separated, and the aqueous phase extracted with EtOAc. The combined organic phases were dried with Na2SO4, filtrated, concentrated under reduced pressure and the obtained material subjected to column chromatography (Si-NH SiO2, DCM/MeOH) to give the title compound (81 mg, 24%). 1H NMR (400 MHz, DMSO-d6) δ [ppm]: 1.29 (t, 3H), 2.46 (s, 3H), 2.87-2.96 (m, 4H), 4.26 (q, 2H), 5.54 (s, 2H), 7.25 (d, 1H), 7.71 (s, 1H), 8.21 (dd, 1H), 8.95 (d, 1H). UPLC-MS (Method 1): Rt = 1.34 min; MS (ESIpos): m/z = 406 [M+H]+.
  • 24
  • [ 1000773-62-5 ]
  • ethyl 8-methyl-4,5-dihydro-1H-furo[2,3-g]indazole-7-carboxylate [ No CAS ]
  • 8-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]methyl}-4,5-dihydro-2H-furo[2,3-g]indazole-7-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / Cooling with ice 1.2: 0.75 h / 20 °C 2.1: lithium hydroxide; water / ethanol; tetrahydrofuran / 70 °C
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