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Product Details of [ 180635-74-9 ]

CAS No. :180635-74-9 MDL No. :MFCD09028744
Formula : C10H11F3O Boiling Point : -
Linear Structure Formula :- InChI Key :RDCHJYSYGXHSQF-UHFFFAOYSA-N
M.W : 204.19 Pubchem ID :22443642
Synonyms :

Calculated chemistry of [ 180635-74-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.19
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 3.78
Log Po/w (MLOGP) : 3.19
Log Po/w (SILICOS-IT) : 3.39
Consensus Log Po/w : 3.07

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 ; 0.0013 mol/l
Class : Soluble
Log S (Ali) : -2.82
Solubility : 0.31 mg/ml ; 0.00152 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.024 mg/ml ; 0.000118 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 180635-74-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 180635-74-9 ]

* 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 [ 180635-74-9 ]

[ 180635-74-9 ] Synthesis Path-Downstream   1~90

  • 2
  • [ 180635-74-9 ]
  • [ 178369-93-2 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 24h;
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 4h; Ice-cooling; 11-2 (11-2) Synthesis of 1-(3-bromopropyl)-4-trifluoromethylbenzene (compound 11-2) Compound 11-1 (9.53 g) was dissolved in methylene chloride (100 ml), triphenylphosphine (13.3 g) and N-bromosuccinimide (8.97 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 3 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (200 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (10.1 g) as a colorless oil. 1H-NMR(CDCl3) δ (ppm): 2.18(2H, quint, J=7.4Hz), 2.85(2H, t, J=7.4Hz), 3.39(2H, t, J=6.4Hz), 7.32(2H, d, J=8.0Hz), 7.55(2H, d, J=8.0Hz).
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 18h; General procedure for obtaining derivatives of (3-Bromopropyl)benzene General procedure: To a stirred solution of 3- or 4-substituted phenylpropanoic acid 51-63 (7.0 mmol) in dry THF (35 ml), borane dimethyl sulfide (21.0 mmol) was added dropwise at 0 oC. The reaction mixture was stirred for 18h at room temperature, quenched with H2O and concentrated in vacuo. The resulting residue was re-dissolved in diethyl ether (25 ml), and washed with 10%NaOH (30ml) and brine. The organic fraction was dried over Na2SO4, filtered, and concentrated in vacuo to give 3-phenylpropan-1-ol derivatives that were used in the next step without further purification. Triphenylphosphine (7.5 mmol) and carbon tetrabromide (7.1 mmol) were added to a stirred solution of the 3-phenylpropan-1-ol derivatives in dry CH2Cl2 at 0 oC. The reaction mixture was stirred for 18h at room temperature and quenched with brine. The organic fraction was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (10:1 n-hexane/EtOAc) to give the corresponding title compound (38-50) in a 64-73% yield (two steps). These are also all known, but commercially unavailable compounds for which the chemical structure of each could be identified from the 1H- and 13C-NMR spectra.
1.0 g With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;

  • 3
  • [ 455-19-6 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran / Heating 2: H2 / 10 percent Pd/C / tetrahydrofuran / 2068.59 Torr 3: LiAlH4 / tetrahydrofuran / 3 h / Heating
  • 5
  • [ 180635-74-9 ]
  • 3-(4-trifluoromethyl-phenyl)-propane-1-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: CBr4; Ph3P / CH2Cl2 / 24 h / 0 °C 2: ethanol / 24 h / Heating 3: NaOH / ethanol / 2 h / Heating
  • 6
  • [ 180635-74-9 ]
  • 2-[3-(4-trifluoromethyl-phenyl)-propyl]-isothiourea; hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CBr4; Ph3P / CH2Cl2 / 24 h / 0 °C 2: ethanol / 24 h / Heating
  • 7
  • [ 180635-74-9 ]
  • 3-[4-(Trifluoromethyl)phenyl]propyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-2-pyrrolidinecarbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: CBr4; Ph3P / CH2Cl2 / 24 h / 0 °C 2: ethanol / 24 h / Heating 3: NaOH / ethanol / 2 h / Heating 4: DCC; DMAP / CH2Cl2 / 24 h / 20 °C
YieldReaction ConditionsOperation in experiment
99%
99%
R.7 3-(4-Trifluoromethylphenyl)-1-propanol (63) 3-(4-Trifluoromethylphenyl)-1-propanol (63) 1H-NMR (270MHz, CDCl3): δ = 7.53 (2H, d, J=7.9 Hz, Ph-H), 7.30 (2H, d, J=7.9 Hz, Ph-H), 3.66 (2H, t, J=6.5 Hz, CH 2OH), 2.76 (2H, t, J=7.8 Hz), 2.74 (1H, br.s, OH), and 1.89 (2H, m).
  • 9
  • [ 53473-36-2 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
100% To an ice-cooled homogeneous solution of 4-(trifluoromethyl)hydrocinnamic acid (9.800 g; 44.918 mmol) in anhydrous THF (250 ml) was added dropwise a solution of 1 M BH3THF (67.4 ml; 67.4 mmol) over 20 min. The resulting homogeneous solution was further stirred at 00C, under nitrogen, for 1 h, and then at rt for 14h. The colorless homogeneous reaction mixture was cooled to 00C, and MeOH (100 ml) was carefully added followed by water (100 ml). MeOH and THF were then removed under vacuum. After extraction with DCM (3 x 100 ml), the combined organic extracts were washed with brine (100 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM / MeOH = 9 / 1 ) to give the pure product 3-(4-trifluoromethyl-phenyl)- propan-1-ol as a colorless oil which was further dried under HV (9.180 g; 100%). LC-MS: tR = 0.89 min.; [M+H]+: no ionisation.
100% With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 70℃; for 16h;Cooling with ice; The carboxylic acid (1 equiv) and sodium borohydride (5 equiv) were suspended in dry tetrahydrofuran. The mixture was cooled in an ice bath and a solution of iodine (2 equiv) in THF was added dropwise over 30 minutes. The mixture was warmed to room temperature and when the solution became clear, it was heated to 70 C for 16 hours. Upon cooling, aqueous 2M sodium hydroxide solution was slowly added and stirred for 1 hour. The mixture was transferred to a seperatory funnel and diluted with ethyl acetate. The aqueous layer was discarded and the organic layer was washed with brine, dried over Na2S04, and filtered. Celite was added and the solvent was evaporated under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.
99% In an inert atmosphere, 3-(4-Trifluoromethyl-phenyl)-propionic acid (10 g, 45.8 mmol) was dissolved in anhydrous THF (250 ml) and cooled to 0 C. followed by the addition of a 1 M solution of borane in THF (69 ml, 69 mmol). Stirring was continued at 0 C. for 1 h and 16 h at rt followed by slow addition of methanol (100 ml) and water (100 ml). The organic solvents were evaporated under reduced pressure. The remaining water phase was extracted with DCM (3×100 ml) and the combined organic layers were washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silicagel, DCM/methanol=9/1 to give 9.25 g (99%) of 3-(4-Trifluoromethyl-phenyl)-propan-1-ol. LC-MS: tR=0.89 min; [M+H]+=no ionisation.
99% With borane; In tetrahydrofuran; at 0 - 20℃; for 17h;Inert atmosphere; In an inert atmosphere, 3-(4-trifluoromethyl-phenyl)-propionic acid (10 g, 45.8 mmol) was dissolved in anhydrous THF (250 ml) and cooled to 0C followed by the addition of a 1 M solution of borane in THF (69 ml, 69 mmol). Stirring was continued at 0C for 1 h and 16 h at rt followed by slow addition of methanol (100 ml) and water (100 ml). The organic solvents were evaporated under reduced pressure. The remaining water phase was extracted with DCM (3 x 100 ml) and the combined organic layers were washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silicagel, DCM / methanol = 9/1 to give 9.25 g (99%) of 3-(4-trifluoromethyl-phenyl)-propan-1-ol. LC-MS: tR = 0.89 min; [M+H]+ = no ionisation.
(11-1) Synthesis of 3-(4-trifluoromethylphenyl)-1-propanol (compound 11-1) 4-Trifluoromethylcinnamic acid (10.0 g) was dissolved in methanol (20 ml) and tetrahydrofuran (50 ml), 10% palladium carbon (5.00 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 10 hr. The reaction container was purged with nitrogen, the solution was filtered, and the filtrate was concentrated to give a colorless powder (10.5 g). The colorless powder was dissolved in tetrahydrofuran (100 ml), and a tetrahydrofuran-borane tetrahydrofuran solution (1 mol/l, 59.5 ml) was added dropwise to the mixture under ice-cooling, and the mixture was stirred under ice-cooling for 30 min, and further at room temperature for 16 hr. To the reaction mixture was added water, 1 mol/l aqueous hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (9.53 g) as a colorless oil. 1H-NMR(CDCl3) delta (ppm): 1.54(1H, brs), 1.87-1.94(2H, m), 2.78(2H, t, J=7.7Hz), 3.68(2H, t, J=6.3Hz), 7.31(2H, d, J=8.0Hz), 7.54(2H, d, J=8.0Hz).
With borane; In tetrahydrofuran; at 0 - 20℃; To an ice-cooled homogeneous solution of 4-(trifluoromethyl)hydrocinnamic acid (20 g, 91.7 mmol 1 eq.) in anhydrous THF (500 ml), a solution of 1M BH3 in THF (137.5 ml, 137.5 mmol, 1.5 eq.) was added dropwise over ca. 20 min. The resulting homogeneous solution was stirred at 0 C. for 1 hour, and further at r.t. for 16 hours. The colorless homogenous reaction mixture was cooled to 0 C., and methanol (200 ml) was carefully added, followed by water (200 ml). Methanol and THF were then removed under vacuum. The product was extracted with dichloromethane (3×200 ml). The combined organic extracts were washed with sat. aq. NaCl soln. (1×100 ml), dried over MgSO4, and concentrated in vacuo. The residue was purified by CC (DCM/MeOH 9:1) to yield the desired alcohol as a colorless oil.LC-MS (A1): tR=0.94 min; no ionization.
To an ice-cooled homogeneous solution of 4-(trifluoromethyl)hydrocinnamic acid (20 g, 91.7 mmol 1 eq.) in anhydrous TetaF (500ml), a solution of IM BH3 in THF (137.5 ml, 137.5 mmol, 1.5 eq.) was added dropwise over ca. 20 min. The resulting homogeneous solution was stirred at 00C for 1 hour, and further at r.t. for 16 hours. The colorless homogenous reaction mixture was cooled to 00C, and methanol (200ml) was carefully added, followed by water (200ml). Methanol and THF were then removed under vacuum. The product was extracted with dichloromethane (3 x 200ml). The combined organic extracts were washed with sat. aq. NaCl soln. (1 x 100ml), dried over MgSO4, and concentrated in vacuo. The residue was purified by CC (DCM/MeOH 9:1) to yield the desired alcohol as a colorless oil. LC-MS (Al): tR = 0.94 min; no ionization.
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 18h; General procedure: To a stirred solution of 3- or 4-substituted phenylpropanoic acid 51-63 (7.0 mmol) in dry THF (35 ml), borane dimethyl sulfide (21.0 mmol) was added dropwise at 0 oC. The reaction mixture was stirred for 18h at room temperature, quenched with H2O and concentrated in vacuo. The resulting residue was re-dissolved in diethyl ether (25 ml), and washed with 10%NaOH (30ml) and brine. The organic fraction was dried over Na2SO4, filtered, and concentrated in vacuo to give 3-phenylpropan-1-ol derivatives that were used in the next step without further purification.

  • 10
  • [ 180635-74-9 ]
  • [ 166947-09-7 ]
YieldReaction ConditionsOperation in experiment
86.5% With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3h; A.3 3-(4-trifluoromethyl-phenyl)-propionaldehyde [general procedure for the oxidation of primary alcohols to aldehydes (GP8)] To an ice-cooled orange suspension of pyridinium chlorochromate (3.659 g; 16.896 mmol) in anhydrous DCM (20 ml) was added dropwise a solution of 3-(4-trifluoromethyl-phenyl)- propan-1-ol (2.300 g; 11.264 mmol) in anhydrous DCM (35 ml). The resulting black suspension was allowed to warm-up to rt and was stirred under nitrogen for 3h. The reaction mixture was directly filtered over silicagel using DCM. After concentration to dryness under reduced pressure, the product 3-(4-trifluoromethyl-phenyl)-propionaldehyde was isolated as a pale yellow oil (1.970 g; 86.5%). LC-MS: tR = 0.95 min.; [M+H]+: no ionisation.
79.31% Stage #1: 3-(4-(trifluoromethyl)phenyl)propan-1-ol With oxalyl dichloride In dichloromethane at -78℃; for 1h; Stage #2: With triethylamine In dichloromethane at -78℃; for 2.5h; 53 Preparation of Compound C13-56-C: To a solution of oxalyl dichloride (1.74 g, 13.72 mmol, 1.20 mL, 2.00 eq) in DCM (15.00 mL) was added dropwise at -78°C. The mixture was stirred at - 78°C for 0.5hr. Then C13-56-B (1.40 g, 6.86 mmol, 1.00 eq) in DCM (15.00 mL) was added dropwise at -78°C. The mixture was stirred at -78°C for 1hr. Then Et3N (3.47 g, 34.30 mmol, 4.75 mL, 5.00 eq) was added dropwise at -78°C. The mixture was stirred at -78°C for 2.5hr to give a yellow suspension. LCMS and TLC(eluting with: PE/EtOAc=2/1) showed the reaction was completed. The reaction mixture was quenched with H2O (30 mL) and extracted with DCM (30 mL*3). The organic layers were dried over Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography on silica gel (eluting with: PE/EtOAc=100%PE to 10/1) to give C13-56-C (1.10 g, 5.44 mmol, 79.31% yield) as a yellow oil. 1H NMR (400MHz, CDCl3): δ 9.85 (s, 1H), 7.72-7.56 (m, 2H), 7.35-7.28 (m, 2H), 3.06-3.01 (m, 2H), 2.86-2.81 (m, 2H).
With pyridinium chlorochromate In dichloromethane at 20℃; for 4h; In an inert atmosphere, 3-(4-trifluoromethyl-phenyl)-propan-1-ol (1.02 g, 5 mmol) was dissolved in DCM (10 ml) and slowly added to a suspension of PCC (1.61 g, 7.5 mmol) in anhydrous DCM (15 ml). Stirring was continued for 4 h at rt. Anhydrous heptane (10 ml) was added to the reaction mixture followed by filtration over a pad of silicagel (15 g). The filtrate was evaporated to give 850 mg of 3-(4-trifluoromethyl-phenyl)-propionaldehyde. LC-MS: tR=0.94 min; [M+H]+=no ionisation.
With pyridinium chlorochromate In dichloromethane at 20℃; for 4h; Inert atmosphere; In an inert atmosphere, 3-(4-trifluoromethyl-phenyl)-propan-1-ol (1.02 g, 5 mmol) was dissolved in DCM (10 ml) and slowly added to a suspension of PCC (1.61 g, 7.5 mmol) in anhydrous DCM (15 ml). Stirring was continued for 4 h at rt. Anhydrous heptane (10 ml) was added to the reaction mixture followed by filtration over a pad of silicagel (15 g). The filtrate was evaporated to give 850 mg of 3-(4-trifluoromethyl-phenyl)-propionaldehyde. LC-MS: tR = 0.94 min; [M+H]+ = no ionisation.
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 15.17h; 83.2 Step 2: To an ice-cooled solution of 3-(4-trifluoromethyl-phenyl)-propan-1-ol (1.02 g, 5.0 mmol, 1 eq.) in DCM (11 mL), pyridinium chlorochromate (1.65 g, 7.5 mmol, 1.5 eq.) was added. The resulting black suspension was stirred at 0° C. for 10 min and further at r.t. for 15 hours. The reaction mixture was directly filtered over a plug of silicagel, eluting with DCM to yield the desired aldehyde as a yellow oil.LC-MS (A1): tR=1.00 min; no ionization.
8.08 g With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Sodium hydrogenocarbonate; sodium bromide In lithium hydroxide monohydrate; ethyl acetate at 0℃; for 1.5h; Preparation of 3-(4-trifluoromethylphenyl)-1-propylaldehyde(3). 3-(4-Trifluoromethylphenyl)-1-propanol (90.6%, 8.27 g, 36.7 mmol) synthesized as described by Sifferlen et al.11) was dissolved in 80 mL of ethyl acetate and sodium hydrogen carbonate (9.38g, 0.112 mol), NaBr (3.83 g, 37.2 mmol), 2,2,6,6-tetramethylpiperidine1-oxyl (0.291 g, 1.86 mmol), and water (80 mL) were added to the mixture at 0 °C. Hypochlorous acid water (13.0%, 21.28 g, 37.2 mmol) was then added dropwise, and the mixture was further stirred for 1.5 h at 0 °C. The product was extracted with ethyl acetate. The organic layer was washed with water (2 × 40 mL) and concentrated in vacuo to give 8.08 g of3-(4-trifluoromethylphenyl)-1-propylaldehyde as a light orange oil.
With pyridinium chlorochromate In dichloromethane at 0℃; for 0.25h;
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 15.1667h; 83.2 To an ice-cooled solution of 3-(4-trifluoromethyl-phenyl)-propan-l-ol (1.02 g, 5.0 mmol, 1 eq.) in DCM (11 mL), pyridinium chlorochromate (1.65 g, 7.5 mmol, 1.5 eq.) was added. The resulting black suspension was stirred at 0 0C for lOmin and further at r.t. for 15 hours. The reaction mixture was directly filtered over a plug of silicagel, eluting with DCM to yield the desired aldehyde as a yellow oil. LC-MS (Al): tR = 1.00 min; no ionization.
With Dess-Martin periodane In dichloromethane at 0 - 20℃; Inert atmosphere;
510 mg With Dess-Martin periodane In dichloromethane at 0 - 20℃; Step 2: 3-[4-(trifluoromethyl)phenyl]propanal 3-[4-(Trifhioromethyl)phenyl]propan-l-ol (750.0 mg, 3.7 mmol, 1.0 equiv.) was dissolved in DCM (8 mL) and cooled to 0 °C, then Dess-Martin reagent (3.1 g, 7.3 mmol, 2.0 equiv.) was added at °C. The reaction mixture was stirred overnight at ambient temperature and then concentrated under vacuum. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1 :9) to give 3-[4-(trifluoromethyl)phenyl]propanal (510.0 mg) as a yellow oil. LCMS Method B-l: [M+H]+= 203.
510 mg With Dess-Martin periodane In dichloromethane at 0 - 20℃; Step 2: 3-[4-(trifluoromethyl)phenyl]propanal 3-[4-(Trifhioromethyl)phenyl]propan-l-ol (750.0 mg, 3.7 mmol, 1.0 equiv.) was dissolved in DCM (8 mL) and cooled to 0 °C, then Dess-Martin reagent (3.1 g, 7.3 mmol, 2.0 equiv.) was added at °C. The reaction mixture was stirred overnight at ambient temperature and then concentrated under vacuum. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1 :9) to give 3-[4-(trifluoromethyl)phenyl]propanal (510.0 mg) as a yellow oil. LCMS Method B-l: [M+H]+= 203.

Reference: [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2008/78291, 2008, A1 Location in patent: Page/Page column 52
[2]Current Patent Assignee: K GEN - WO2021/62030, 2021, A1 Location in patent: Paragraph 0565; 0568; 0569
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - US2009/99228, 2009, A1 Location in patent: Page/Page column 10; 17
[4]Current Patent Assignee: JOHNSON & JOHNSON INC - EP2013209, 2011, B1 Location in patent: Page/Page column 21
[5]Current Patent Assignee: JOHNSON & JOHNSON INC - US2011/86889, 2011, A1 Location in patent: Page/Page column 24
[6]Nishihachijo, Masakatsu; Hirai, Yoshinori; Kawano, Shigeru; Nishiyama, Akira; Minami, Hiromichi; Katayama, Takane; Yasohara, Yoshihiko; Sato, Fumihiko; Kumagai, Hidehiko [Bioscience, Biotechnology and Biochemistry, 2014, vol. 78, # 4, p. 701 - 707]
[7]Welin, Eric R.; Warkentin, Alexander A.; Conrad, Jay C.; MacMillan, David W. C. [Angewandte Chemie - International Edition, 2015, vol. 54, # 33, p. 9668 - 9672][Angew. Chem., 2015, vol. 127, # 33, p. 9804 - 9808,5]
[8]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2009/150614, 2009, A1 Location in patent: Page/Page column 57
[9]Nouaille, Augustin; Pannecoucke, Xavier; Poisson, Thomas; Couve-Bonnaire, Samuel [Advanced Synthesis and Catalysis, 2021, vol. 363, # 8, p. 2140 - 2147]
[10]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2022/15975, 2022, A1 Location in patent: Page/Page column 150
[11]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2022/15975, 2022, A1 Location in patent: Page/Page column 150
  • 11
  • [ 180635-74-9 ]
  • [ 1042906-15-9 ]
YieldReaction ConditionsOperation in experiment
66% With formic acid; isocyanate de chlorosulfonyle; triethylamine In dichloromethane at 0 - 25℃; Schlenk technique; Inert atmosphere;
63% With pyridine; formic acid; isocyanate de chlorosulfonyle In dichloromethane
  • 12
  • [ 180635-74-9 ]
  • 2-{1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl}-N-methyl-2-phenyl-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: acetic acid / ethanol / 0.1 h / 130 °C / 10501.1 Torr / microwave irradiation 3: N-ethyl-N,N-diisopropylamine / 3-methyl-2-butyl-ketone / 24 h / 90 °C / Inert atmosphere
  • 13
  • [ 180635-74-9 ]
  • [ 955403-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: acetic acid / ethanol / 0.1 h / 130 °C / 10501.1 Torr / microwave irradiation
  • 14
  • [ 180635-74-9 ]
  • C18H18F3NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / ethyl acetate; water / 1.5 h / 0 °C 2: recombinant norcoclaurine synthase from Coptis japonica, first 29 amino acid residues removed / dimethyl sulfoxide / 0.25 h / 30 °C / pH 7 / Enzymatic reaction
  • 15
  • [ 180635-74-9 ]
  • (R)-3-(4-trifluoromethylbenzyl)-4-oxobutyronitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 0.25 h / 0 °C 2: (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one trifluoromethanesulfonate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 2,6-dimethylpyridine / dimethyl sulfoxide / 8 h / 23 °C / Inert atmosphere; Sealed tube; Irradiation
  • 16
  • [ 180635-74-9 ]
  • 3-(4-trifluoromethylbenzyl)-4-oxobutyronitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 0.25 h / 0 °C 2: C9H18N2O*CHF3O3S; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 2,6-dimethylpyridine / dimethyl sulfoxide / 8 h / 23 °C / Inert atmosphere; Sealed tube; Irradiation
  • 17
  • [ 180635-74-9 ]
  • C12H12F3NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridinium chlorochromate / dichloromethane / 0.25 h / 0 °C 2: (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one trifluoromethanesulfonate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 2,6-dimethylpyridine / dimethyl sulfoxide / 8 h / 23 °C / Inert atmosphere; Sealed tube; Irradiation 3: sodium tetrahydroborate / dichloromethane; methanol / 3 h / 0 °C
  • 18
  • [ 455-13-0 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; lithium chloride; tetrabutylammomium bromide; lithium acetate dihydrate / N,N-dimethyl-formamide / 48 h / 20 °C 2: sodium tetrahydroborate / methanol / 0.17 h / 20 °C
  • 19
  • [ 166947-09-7 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
253 mg With sodium tetrahydroborate In methanol at 20℃; for 0.166667h;
  • 20
  • [ 180635-74-9 ]
  • [ 95123-61-8 ]
YieldReaction ConditionsOperation in experiment
92% With (S)-diphenylprolinol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide; acetonitrile at 20℃; for 6h; stereoselective reaction;
  • 21
  • [ 1208-64-6 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 20 - 70℃; for 16.5h;Cooling with ice; The carboxylic acid (1 equiv) and sodium borohydride (5 equiv) were suspended in dry tetrahydrofuran. The mixture was cooled in an ice bath and a solution of iodine (2 equiv) in THF was added drop wise over 30 minutes. The mixture was warmed to room temperature and when the solution became clear, it was heated to 70 C for 16 hours. Upon cooling, aqueous 2M sodium hydroxide solution was slowly added and stirred for 1 hour. The mixture was transferred to a seperatory funnel and diluted with ethyl acetate. The aqueous layer was discarded and the organic layer was washed with brine, dried over Na2SC>4, and filtered. Celite was added and the solvent was evaporated under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.
  • 22
  • [ 98-88-4 ]
  • [ 180635-74-9 ]
  • 3-(4-trifluoromethylphenyl)propyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With pyridine In dichloromethane at 0 - 20℃; for 5h; 3-(4-Methoxyphenyl)propyl Benzoate (36c) General procedure: To a solution of 3-(4-methoxyphenyl)-1-propanol 42c(1.66 g, 10.0 mmol) in CH2Cl2 (20 mL), BzCl (1.39 mL,12.0 mol) and pyridine (1.93 mL, 24.0 mmmol) were added at0°C. The reaction mixture was stirred for 1 h at the same temperature,and for 2 h at rt. The mixture was cooled to 0°C, andsat. NaHCO3 aq. was added. The phases were separated. Theorganic layer was washed with H2O, 1 N HCl aq., H2O, andbrine, dried over Na2SO4, filtered, and evaporated under reducedpressure. The residue was purified with flash columnchromatography (SiO2, n-hexane-EtOAc=19 : 19 : 1) to affordbenzoate 36c (1.69 g, 63%).
  • 23
  • [ 98-88-4 ]
  • [ 180635-74-9 ]
  • 3-oxo-3-(4-trifluoromethylphenyl)propyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 5 h / 0 - 20 °C 2: cobalt(II) acetate; manganese(III) triacetate dihydrate; oxygen; 4,5,6,7-tetrafluoro-2-hydroxy-3-(2,2,2-trifluoroethoxy)-3-trifluoromethylisoindolin-1-one / 2,2,2-trifluoroethanol / 48 h / 60 °C / 760.05 Torr
  • 24
  • [ 16466-61-8 ]
  • [ 180635-74-9 ]
  • (S)-di-tert-butyl 1-(1-hydroxy-3-(4-(trifluoromethyl)phenyl)propan-2-yl)hydrazine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 1,2-bis(t-butyloxycarbonyl)hydrazine; 3-(4-(trifluoromethyl)phenyl)propan-1-ol With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,6-dimethylpyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) bromide In acetonitrile at 20℃; for 72h; Stage #2: In methanol; acetonitrile at 0℃; enantioselective reaction;
  • 25
  • [ 16466-61-8 ]
  • [ 180635-74-9 ]
  • C27H32F3N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: copper(I) bromide; 2,6-dimethylpyridine; (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 72 h / 20 °C 1.2: 0 °C 2.1: pyridine / dichloromethane
  • 26
  • [ 180635-74-9 ]
  • 4-(4-(Trifluoromethyl)phenyl)butanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux
  • 27
  • [ 180635-74-9 ]
  • 4-(4-(trifluoromethyl)phenyl)butanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C
  • 28
  • [ 180635-74-9 ]
  • C13H13F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: 4-methyl-morpholine / 80 °C
  • 29
  • [ 180635-74-9 ]
  • C13H15F3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: 4-methyl-morpholine / 80 °C 5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C
  • 30
  • [ 180635-74-9 ]
  • ((E)-6-(4-(trifluoromethyl)phenyl)hex-3-enyloxy)(tert-butyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: 4-methyl-morpholine / 80 °C 5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 6: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C
  • 31
  • [ 180635-74-9 ]
  • C14H15F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran
  • 32
  • [ 180635-74-9 ]
  • C12H13F3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C
  • 33
  • [ 180635-74-9 ]
  • C12H12ClF3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane
  • 34
  • [ 180635-74-9 ]
  • C13H12F3N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile
  • 35
  • [ 180635-74-9 ]
  • C13H16F3N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride
  • 36
  • [ 180635-74-9 ]
  • (3aRS,9bSR)-8-(trifluoromethyl)-1,2,3a,4,5,9b-Hexahydronaphtho[2,1-b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: 4-methyl-morpholine / 80 °C 5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 6: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C 7: [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate / dichloromethane / 2.5 h / -80 °C
  • 37
  • [ 180635-74-9 ]
  • (3aR,9bS)-8-(trifluoromethyl)-1,2,3a,4,5,9b-hexahydronaphtho[2,1-b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: 4-methyl-morpholine / 80 °C 5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 6: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C 7: boron trifluoride diethyl etherate; (R)-tert-butyl 2-[2-(diacetoxyiodo)phenoxy]propanoate / 1 h / -80 °C
  • 38
  • [ 180635-74-9 ]
  • (3aR,9bS)-8-(trifluoromethyl)-1,2,3a,4,5,9b-hexahydronaphtho[2,1-b]furan [ No CAS ]
  • (3aS,9bR)-8-(trifluoromethyl)-1,2,3a,4,5,9b-hexahydronaphtho[2,1-b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: 4-methyl-morpholine / 80 °C 5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 6: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C 7: boron trifluoride diethyl etherate; dimethyl-2,2'-((2-(diacetoxy-λ3-iodanyl)-1,3-phenylene)bis(oxy))(2R,2'R)-dipropionate / 1 h / -80 °C
  • 39
  • [ 180635-74-9 ]
  • (E)-N-methanesulfonyl-6-(4-trifluoromethyphenyl)hex-3-en-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride 9: triethylamine / dichloromethane / 3 h / 0 - 20 °C
  • 40
  • [ 180635-74-9 ]
  • (E)-N-(2-nitrophenyl)sulfonyl-6-(4-trifluoromethyphenyl)hex-3-en-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride 9: triethylamine / dichloromethane / 3 h / 0 - 20 °C
  • 41
  • [ 180635-74-9 ]
  • C14H16F3NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride 9: triethylamine / dichloromethane / 3 h / 0 - 20 °C 10: [bis(acetoxy)iodo]benzene; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / -80 °C
  • 42
  • [ 180635-74-9 ]
  • C14H16F3NO2S [ No CAS ]
  • C14H16F3NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride 9: triethylamine / dichloromethane / 3 h / 0 - 20 °C 10: (R)-tert-butyl 2-[2-(diacetoxyiodo)phenoxy]propanoate; trimethylsilyl trifluoromethanesulfonate / 3.5 h / -80 °C
  • 43
  • [ 180635-74-9 ]
  • C19H17F3N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride 9: triethylamine / dichloromethane / 3 h / 0 - 20 °C 10: [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate / dichloromethane / 6 h / -80 °C
  • 44
  • [ 180635-74-9 ]
  • C19H17F3N2O4S [ No CAS ]
  • C19H17F3N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: triethylamine / dichloromethane / 0 °C 2: dimethyl sulfoxide; water / Reflux 3: diisobutylaluminium hydride / dichloromethane / 3 h / -78 °C 4: n-butyllithium / tetrahydrofuran 5: diisobutylaluminium hydride / 0 °C 6: triphenylphosphine; tetrachloromethane 7: copper(l) iodide / acetonitrile 8: lithium aluminium tetrahydride 9: triethylamine / dichloromethane / 3 h / 0 - 20 °C 10: (R)-tert-butyl 2-[2-(diacetoxyiodo)phenoxy]propanoate; trimethylsilyl trifluoromethanesulfonate / 3.5 h / -80 °C
  • 45
  • [ 124-63-0 ]
  • [ 180635-74-9 ]
  • C11H13F3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃;
  • 46
  • [ 358-23-6 ]
  • [ 180635-74-9 ]
  • 3-(4-trifluoromethylphenyl)-1-propyl trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With 2,4-lutidine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;
  • 47
  • [ 180635-74-9 ]
  • (4E)-1-(5-iodo-4-pentenyl)-4-trifluoromethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 - 0 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / 1 h / Inert atmosphere 4.1: zirconocene dichloride; lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 4.2: 0.25 h / 20 °C / Inert atmosphere
  • 48
  • [ 180635-74-9 ]
  • 1-(trifluoromethyl)-4-[(4E)-8-[(triisopropylsilyl)oxy]-4-octenyl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 - 0 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / 1 h / Inert atmosphere 4.1: zirconocene dichloride; lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 4.2: 0.25 h / 20 °C / Inert atmosphere 5.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 5.2: 0 - 20 °C / Inert atmosphere
  • 49
  • [ 180635-74-9 ]
  • 1-(trifluoromethyl)-4-[(4E)-8-[(triisopropylsilyl)oxy]-4-octenyl]benzene [ No CAS ]
  • 1-(trifluoromethyl)-4-[[trans-8-[(triisopropylsilyl)oxy]propyl]cyclopropylethyl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2: benzene-d6 / 25 °C / Inert atmosphere; Glovebox; Darkness
  • 50
  • [ 180635-74-9 ]
  • 1-(trifluoromethyl)-4-[(3E)-7-[(triisopropylsilyl)oxy]-3-heptenyl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 - 0 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / 1 h / Inert atmosphere 4.1: zirconocene dichloride; lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 4.2: 0.25 h / 20 °C / Inert atmosphere 5.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 5.2: 0 - 20 °C / Inert atmosphere
  • 51
  • [ 180635-74-9 ]
  • 1-(trifluoromethyl)-4-[[trans-8-[(triisopropylsilyl)oxy]propyl]cyclopropylethyl]benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 - 0 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / 1 h / Inert atmosphere 4.1: zirconocene dichloride; lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 4.2: 0.25 h / 20 °C / Inert atmosphere 5.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 5.2: 0 - 20 °C / Inert atmosphere 6.1: diethylzinc / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 6.2: 1.17 h / 0 °C / Inert atmosphere
  • 52
  • [ 180635-74-9 ]
  • 1-[(5-trimethylsilyl)pentyn-4-yl]-4-trifluoromethyl benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 - 0 °C / Inert atmosphere
  • 53
  • [ 180635-74-9 ]
  • [ 1549791-99-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 2,4-lutidine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere 2.2: 1 h / -78 - 0 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / 1 h / Inert atmosphere
  • 54
  • [ 173546-21-9 ]
  • [ 826994-11-0 ]
  • [ 125617-18-7 ]
  • [ 180635-74-9 ]
  • 55
  • [ 455-13-0 ]
  • [ 826994-11-0 ]
  • [ 125617-18-7 ]
  • [ 180635-74-9 ]
  • 56
  • [ 20754-22-7 ]
  • [ 125617-18-7 ]
  • [ 180635-74-9 ]
  • 57
  • [ 705-31-7 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) chloride; bathophenanthroline / dimethyl sulfoxide / 12 h / 20 °C / 11251.1 Torr / Inert atmosphere; Autoclave 2: hydrogen / methanol / 18 h / 20 °C / 7500.75 Torr / Autoclave 3: hydrogen; molybdenum hexacarbonyl / 1-methyl-pyrrolidin-2-one / 14 h / 180 °C / 52505.3 Torr / Autoclave
  • 58
  • C10H5F3O2*C9H19N [ No CAS ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen / methanol / 18 h / 20 °C / 7500.75 Torr / Autoclave 2: hydrogen; molybdenum hexacarbonyl / 1-methyl-pyrrolidin-2-one / 14 h / 180 °C / 52505.3 Torr / Autoclave
  • 59
  • C10H9F3O2*C9H19N [ No CAS ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
280 mg With hydrogen; molybdenum hexacarbonyl In 1-methyl-pyrrolidin-2-one at 180℃; for 14h; Autoclave;
  • 60
  • [ 455-13-0 ]
  • [ 107-18-6 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
67% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tetramethylammonium formiate; triphenylphosphine In water; N,N-dimethyl-formamide at 80℃; for 4h; regioselective reaction;
  • 61
  • [ 180635-74-9 ]
  • 1-(3-iodopropyl)-4-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 1h; Sealed tube;
  • 62
  • [ 180635-74-9 ]
  • (2S,3S,4R)-1-{2,3,6-tri-O-(p-methoxybenzyl)-4-O-[3-(4-trifluoromethylphenyl)propyl]-α-D-galactopyranosyloxy}-2-azido-3,4-di-O-(p-methoxybenzyl)octadecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 1 h / 0 - 20 °C / Sealed tube 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 17 h / 0 - 20 °C / Sealed tube
  • 63
  • [ 180635-74-9 ]
  • C74H98F3NO13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 1 h / 0 - 20 °C / Sealed tube 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 17 h / 0 - 20 °C / Sealed tube 3: pyridine; hydrogen sulfide / water / 48 h / 20 °C / Sealed tube
  • 64
  • [ 180635-74-9 ]
  • [ 1126527-72-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: isocyanate de chlorosulfonyle; formic acid; triethylamine / dichloromethane / 0 - 25 °C / Schlenk technique; Inert atmosphere 2: C24H26FeN6(2+)*2ClO4(1-); [2,2]bipyridinyl; bis(tertbutylcarbonyloxy)iodobenzene / acetonitrile / 2 h / 80 °C / Glovebox; Inert atmosphere; Molecular sieve
  • 65
  • [ 180635-74-9 ]
  • 3-(2-hydroxy-2,2-diphenylacetoxy)-1-{3-[4-(trifluoromethyl)phenyl]propyl}-1-azoniabicyclo[2.2.2]octane bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 18 h / 0 - 20 °C 2: 1,4-dioxane / 168 h / 20 °C
  • 66
  • [ 180635-74-9 ]
  • C30H27F3NO5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: silica gel; pyridinium chlorochromate / dichloromethane / 20 °C 2: acetic acid / 80 - 90 °C
  • 67
  • [ 180635-74-9 ]
  • C20H18F6O2 [ No CAS ]
  • [ 166947-09-7 ]
YieldReaction ConditionsOperation in experiment
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃;
  • 68
  • [ 349-95-1 ]
  • [ 64-17-5 ]
  • [ 180635-74-9 ]
YieldReaction ConditionsOperation in experiment
37% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium <i>tert</i>-butylate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere;
  • 69
  • [ 115262-01-6 ]
  • [ 180635-74-9 ]
  • 1-(3-(difluoromethoxy)propyl)-4-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydrogenfluoride In water at 20℃; for 12h; Typical Procedures (Method 6.1) General procedure: Into a 10-mL plastic tube containing 2-phenylethanol (1a) (61 mg, 0.5 mmol) and KHF 2 (156 mg, 2.0 mmol) was added water (0.3 mL). After stirring for a while to dissolve KHF 2 , TMSCF 2 Br (2) (156 μL, 1.0 mmol) was added. The reaction mixture was vigorously stirred at room temperature for 2 h, and then diluted with CH2Cl2 (2.0 mL) for determination of the 19F NMR yield. For characterization of the product, the above reaction mixture was further treated with water (2.0 mL) and extracted with CH2Cl2 (3 × 2.0 mL). The organic layers were combined and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel (heptane/CH 2 Cl 2 , 5:1, v/v) to afford the desired product 3a in 77% yield (66 mg).
  • 70
  • [ 180635-74-9 ]
  • methyl (Z)-2-fluoro-5-(4-(trifluoromethyl)phenyl)pent-2-enoate [ No CAS ]
  • C14H14F4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 3.1: [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) / dichloromethane / 15 h / 80 °C / Inert atmosphere; Sealed tube
  • 71
  • [ 180635-74-9 ]
  • 1-(but-3-en-1-yl)-4-(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere
  • 72
  • [ 180635-74-9 ]
  • C54H61NO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: oxalyl dichloride / dichloromethane / 1 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: ammonia / ethanol / 70 h / 10 °C 3.1: sodium hydroxide / 2 h / 40 °C 3.2: 3 h / 90 °C 4.1: 12 h / 10 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; benzotriazol-1-ol / dichloromethane / 12 h / 40 °C
  • 73
  • [ 180635-74-9 ]
  • C30H39NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: oxalyl dichloride / dichloromethane / 1 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: ammonia / ethanol / 70 h / 10 °C 3.1: sodium hydroxide / 2 h / 40 °C 3.2: 3 h / 90 °C 4.1: 12 h / 10 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; benzotriazol-1-ol / dichloromethane / 12 h / 40 °C 6.1: trifluoroacetic acid; triethylsilane / tetrahydrofuran / 12 h / 10 °C
  • 74
  • [ 180635-74-9 ]
  • C30H39NO6 [ No CAS ]
  • C30H39NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: oxalyl dichloride / dichloromethane / 1 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: ammonia / ethanol / 70 h / 10 °C 3.1: sodium hydroxide / 2 h / 40 °C 3.2: 3 h / 90 °C 4.1: 12 h / 10 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; benzotriazol-1-ol / dichloromethane / 12 h / 40 °C 6.1: trifluoroacetic acid; triethylsilane / tetrahydrofuran / 12 h / 10 °C 7.1: methanol; ethyl acetate / Resolution of racemate
  • 75
  • [ 180635-74-9 ]
  • C11H11F3N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / dichloromethane / 1 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: ammonia / ethanol / 70 h / 10 °C
  • 76
  • [ 180635-74-9 ]
  • C11H12F3NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / dichloromethane / 1 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: ammonia / ethanol / 70 h / 10 °C 3.1: sodium hydroxide / 2 h / 40 °C 3.2: 3 h / 90 °C
  • 77
  • [ 180635-74-9 ]
  • C16H20F3NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / dichloromethane / 1 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: ammonia / ethanol / 70 h / 10 °C 3.1: sodium hydroxide / 2 h / 40 °C 3.2: 3 h / 90 °C 4.1: 12 h / 10 °C
  • 78
  • [ 180635-74-9 ]
  • 1‐(3‐chloropropyl)‐4‐(trifluoromethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With bis(trichloromethyl) carbonate; triethylamine In dichloromethane at 0 - 20℃; for 6h; 1-(3-Chloropropyl)-4-(trifluoromethyl)benzene (9o). Triethylamine (2.5 mmol) was added to asolution of 13 (1.0 mmol) in anhydrous dichloromethane (10 mL) at 0 °C, followed bytriphosgene (0.5 mmol) in one portion. The mixture was stirred at 0 °C for 5 minutes andthen allowed to warm to room temperature. After the reaction was complete, the reactionmixture was poured into an aqueous solution containing saturated sodium bicarbonate.After separation of the layers, the aqueous layer was extracted again with dichloromethane(2 × 30 mL). Then, the organic layers were combined, dried with MgSO4, filtered,and concentrated in vacuo, and the crude product was purified on a silica gel column toobtain compound 9o. White solid. Yield, 71%. 1H-NMR (400 MHz, CDCl3) δ 7.58 (d, J = 8.0Hz, 2H), 7.34 (d, J = 7.9 Hz, 2H), 3.55 (t, J = 6.4 Hz, 2H), 2.88 (t, J = 7.5 Hz, 2H), 2.17-2.06(m, 2H).
  • 79
  • [ 180635-74-9 ]
  • 5‐methoxy‐2‐(3‐(4‐(trifluoromethyl)phenyl)propoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 6 h / 0 - 20 °C 2: potassium carbonate / acetonitrile / 5 h / 80 °C
  • 80
  • [ 180635-74-9 ]
  • 6‐amino‐4‐(5‐methoxy‐2‐(3‐(4‐(trifluoromethyl)phenyl)propoxy)phenyl)‐3‐methyl‐1,4‐dihydropyrano[2,3‐c]pyrazole‐5‐carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 6 h / 0 - 20 °C 2.1: potassium carbonate / acetonitrile / 5 h / 80 °C 3.1: triethylamine / ethanol / 0.08 h / Heating 3.2: 0.25 h / Heating
  • 81
  • [ 38857-88-4 ]
  • [ 180635-74-9 ]
  • C16H15Cl6F3N2O5 [ No CAS ]
  • C16H13Cl6F3N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 66% 2: 6% With N-hydroxyphthalimide; 1,1,1,3',3',3'-hexafluoro-propanol at 60℃; for 24h; Inert atmosphere; chemoselective reaction;
  • 82
  • [ 180635-74-9 ]
  • 1-chloro-2-fluoro-3-(1-(4-(trifluoromethyl)phenyl)propyl)benzene [ No CAS ]
  • C16H13ClF4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.67 h / Inert atmosphere 2.2: 0.17 h / Inert atmosphere 3.1: [Pd(μ-I)(Cy2PtBu)]2 / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.17 h / 20 °C / Inert atmosphere
  • 83
  • [ 180635-74-9 ]
  • C10H10ClF3Zn [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.67 h / Inert atmosphere 2.2: 0.17 h / Inert atmosphere
  • 84
  • [ 180635-74-9 ]
  • 2-fluoro-3-(1-(4-(trifluoromethyl)phenyl)propyl)pyridine [ No CAS ]
  • C15H13F4N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.67 h / Inert atmosphere 2.2: 0.17 h / Inert atmosphere 3.1: [Pd(μ-I)(Cy2PtBu)]2 / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.17 h / 20 °C / Inert atmosphere
  • 85
  • [ 180635-74-9 ]
  • N-[3-[4-(trifluoromethyl)phenyl]propylidene]hydroxylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: hydroxyamino hydrochloride; sodium hydroxide / ethanol; lithium hydroxide monohydrate / 2 h / 90 °C
  • 86
  • [ 180635-74-9 ]
  • N-hydroxy-3-[4-(trifluoromethyl)phenyl]propanecarbonimidoyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: hydroxyamino hydrochloride; sodium hydroxide / ethanol; lithium hydroxide monohydrate / 2 h / 90 °C 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 50 °C
  • 87
  • [ 180635-74-9 ]
  • methyl 3-[2-[4-(trifluoromethyl)phenyl]ethyl]-1,2-oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: hydroxyamino hydrochloride; sodium hydroxide / ethanol; lithium hydroxide monohydrate / 2 h / 90 °C 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 50 °C 4: sodium hydroxide / chloroform / 20 °C
  • 88
  • [ 180635-74-9 ]
  • 3-[2-[4-(trifluoromethyl)phenyl]ethyl]-1,2-oxazole-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Dess-Martin periodane / dichloromethane / 0 - 20 °C 2: hydroxyamino hydrochloride; sodium hydroxide / ethanol; lithium hydroxide monohydrate / 2 h / 90 °C 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 50 °C 4: sodium hydroxide / chloroform / 20 °C 5: sodium hydroxide; lithium hydroxide monohydrate / methanol / 2 h / 80 °C
  • 89
  • [ 115665-91-3 ]
  • [ 180635-74-9 ]
  • methyl (E)-4-(5-(4-(trifluoromethyl)phenyl)pent-1-en-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tris(4-methoxyphenyl)phosphane In 1,4-dioxane; 1,2-dimethoxyethane; acetonitrile at 40℃; for 24h; Inert atmosphere; Molecular sieve; Sealed tube; Irradiation; chemoselective reaction;
  • 90
  • [ 75-15-0 ]
  • [ 180635-74-9 ]
  • C11H10F3OS2(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-(4-(trifluoromethyl)phenyl)propan-1-ol With potassium-t-butoxide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: carbon disulfide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Sealed tube;
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