Home Cart 0 Sign in  
X

[ CAS No. 124276-83-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 124276-83-1
Chemical Structure| 124276-83-1
Chemical Structure| 124276-83-1
Structure of 124276-83-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 124276-83-1 ]

Related Doc. of [ 124276-83-1 ]

Alternatived Products of [ 124276-83-1 ]

Product Details of [ 124276-83-1 ]

CAS No. :124276-83-1 MDL No. :MFCD07374414
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :VHNBUFCWKWBTIZ-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :20026178
Synonyms :

Calculated chemistry of [ 124276-83-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.05
TPSA : 23.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 2.94
Log Po/w (MLOGP) : 2.71
Log Po/w (SILICOS-IT) : 3.52
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) : -3.17
Solubility : 0.152 mg/ml ; 0.000684 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.387 mg/ml ; 0.00174 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0153 mg/ml ; 0.000069 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 124276-83-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 124276-83-1 ]

* 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 [ 124276-83-1 ]

[ 124276-83-1 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 124276-83-1 ]
  • [ 597563-13-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; dihydrogen peroxide In methanol; water at 55℃; for 5h; 1.B Part (B) -Preparation of bromoamide (3) The bromophenylcyclopropylnitrile, [( (2),] part (A), 5.9 g; 26.6 mmol), is dissolved in methanol (150 ml). Potassium hydroxide [(25%] aqueous solution, 0.68 ml) and hydrogen peroxide [(30%,] 35 ml) are added and the reaction mixture is heated at [55°] for 5 hr. The mixture is concentrated to give the crude bromoamide.
  • 2
  • [ 31938-07-5 ]
  • [ 107-04-0 ]
  • [ 124276-83-1 ]
YieldReaction ConditionsOperation in experiment
97% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In water; at 60℃; for 16.5h; 3-Bromophenylacetonitrile (1 eq.), 1-bromo-2-chloroethane (1.5 eq.) and benzyl triethylammonium chloride (0.08 eq.) were placed into a 5 L 3-neck round buttom flask and stirred for 15 min. A solution of 50% aq sodium hydroxide (6 eq.) was added over 30 min. The reaction was heated at 60 C for 16 h. IPC showed 100% completion. The reaction was cooled to rt and water (3.3 vol) and CH2CI2 (3.3 vol) were added and layers separated. The aqueous layer was further extracted with CH2CI2 (3.3 vol) and combined organics washed with water (3.3 vol), 1 M HCI (3.3 vol) and brine (3. 3vol). The organic layer was dried (MgSC ), filtered and concentrated under reduced pressure. The crude product was purified by distillation to give clean product (95-97%). 1H NMR (300 MHz, CDCI3) delta: 1.36-1.51 (m, 2 H), 1.70-1.85 (m, 2 H), 7.22-7.29 (m, 2 H), 7.41-7.48 (m, 2 H).
68% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In water; at 10 - 55℃; for 20h; 25 g (0.13 Mol) 3-Brom-benzylcyanid werden in 32 ml (0.38 Mol) 1-Brom-2-chlor-ethan aufgenommen und mit 0.6 g (2.6 mMol) Benzyltriethylammoniumchlorid versetzt. Anschlieend wird eine Lsung von 105.8 g (2.65 Mol) Natriumhydroxid in 106 ml Wasser bei 10 bis 25C zugetropft. Nach 20 Stunden bei 55C wird die Reaktionslsung auf Eiswasser gegossen und mit Essigester extrahiert. Die organischen Extrakte werden getrocknet und eingedampft. Der Rckstand wird mit Petrolether verrieben, abgesaugt und getrocknet. Ausbeute: 19.3 g (68 % der Theorie), Rf-Wert: 0.69 (Petrolether/Essigester = 4:1)
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In water; at 20 - 80℃; for 3.3h; A mixture of [L-BROMO-2-CHLOROETHANE] (120 ml), 3-bromobenzyl cyanide (1,25 g) and benzyl-triethylammonium chloride [(1.] [1] g) is stirred at [40] while aqueous sodium hydroxide (50%, 120 g) is added dropwise over approximately 20 min. The reaction temperature rises to about [80] during the addition of the aqueous base. The reaction mixture is stirred very vigorous while the temperature slowly drops to [50] (over about 3 hr). After 3 hours, the reaction mixture is cooled down to [20-25,] water (100 ml) is added and the mixture stirred for 5 min. The organic phase is separated and the aqueous phase is extracted with dichloromethane (3 x). The combined organic phases are washed with water and dilute hydrochloric acid. The organic phase is then dried over magnesium sulfate, filtered and concentrated. The concentrate is purified by a high vacuum fractionation using short-path set-up and single receiver. The fractions with bp = [108-115/0.] 1-0.05 mm Hg are collected; after cooling to [20-25] this liquid solidified.
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In water; at 20 - 60℃; EXAMPLE 10; 1- [4'-[(1S)-1-[[(1S)-1-[[(1-cyanocyclopropyl)amino]carbonyl]-3-fluoro-3-methylbutyl]amino]-2,2,2- TRIFLUOROETHYLL F L, 1 -BIPHENYLL-3-YLL- CYCLOPROPANECARBOXYLIC acid; Step 1 : 1-(3-bromophenyl) cyclopropanecarbonitrile; To a room temperature solution of 3-bromophenylacetonitrile (15.0 g) in a solution of 18.4 mL of sodium hydroxide (50% in water w/w) were added 1-bromo-2-chloroethane and (9.5 mL) and benzyltriethylammonium chloride (522 mg). The mixture was heated at 60 C overnight. The reaction mixture was cooled to room temperature and diethyl ether was added (300 ML) and partitioned. The ether LAYER WAS WASHED WITH WATER (100 ML), 10% AQ. HC1 (100 ML) AND BRINE, THEN DRIED OVER MAGNESIUM sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound. H NMR (CD3COCD3) 8 7.56 (1H, s), 7.53 (1H, d), 7.36-7. 43 (2H, m), 1.79-1. 83 (2H, m), 1.58-1. 64 (2H, M).
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In water; at 20 - 50℃; for 12h; General procedure: To a flask charged with a magnetic stir bar and the arylacetonitrile (S5) (6.6 mmol) was added 1-bromo-2-chloroethane (9.9 mmol), benzyltriethylammonium chloride (0.132 mmol), and 50% aqueous sodium hydroxide (39.6 mmol). The resulting solution was stirred at 50 C under a reflux condenser and ambient atmosphere for 12 h. The solution was poured into water and extracted with dichloromethane twice. The combined organic extracts were washed with 3 N HCI, saturated aqueous NaHCO3, and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the desired 1-aryl- 1-cyanocyclopropane product (S6), typically in sufficient purity to be carried forward without further purification to the next step.

  • 3
  • [ 124276-83-1 ]
  • [ 124276-95-5 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 1-(3-bromophenyl)cyclopropane-1-carbonitrile With water; potassium hydroxide In ethylene glycol at 140℃; for 4.5h; Stage #2: In ethylene glycol 2.b b. 1-(3-Brom-phenyl)-cyclopropancarbonsure 7.6 g (0.135 Mol) Kaliumhydroxid werden in 60 ml Ethylenglykol gelst, portionsweise mit 10.0 g (0.045 Mol) 1-(3-Brom-phenyl)-1-cyclopropan-nitril versetzt und nach Zugabe von 30 ml Wasser 4.5 Stunden auf 140C erhitzt. Nach Abkhlung wird auf 600 ml Eiswasser gegossen und mit Ether extrahiert. Die wssrige Phase wird auf Eis/konz. Salzsure gegossen, das ausgefallene Produkt abgesaugt und getrocknet. Ausbeute: 10.1 g (93 % der Theorie), Rf-Wert: 0.85 (Kieselgel; Cyclohexan/Essigester/Eisessig = 1:1:0.01)
92% With water; lithium hydroxide at 110℃; for 16h; 5.2 5.2 1-(3-Bromo-phenyl)cyclopropane-1-carboxylic acid 1-(3-bromo-phenyl)cyclopropane-1-carbonitrile (1 eq.), lithium hydroxide (2 eq.) and water (6.0 vol) was placed into a 5 L 3-neck round bottom flask. The reaction was heated at reflux (1 10°C) for 16 h. The reaction was cooled to rt and diluted with water (5 vol). The aqueous was washed with CH2CI2 (2 x 3vol) and then the aqueous was acidified to pH 3 using concentrated HCI (~1 vol). This was then extracted with MTBE (2 x 3 vol), dried (MgSCU), filtered and concentrated under reduced pressure to give a white crystalline powder (-92%). 1H NMR (300 MHz, CDCI3) δ: 1.21-1.35 (m, 2 H), 1.62-1.76 (m, 2 H), 7.17-7.22 (m, 1 H), 7.28-7.31 (m, 1 H), 7.40-7.47 (m, 1 H), 7.51-7.52 (m, 1 H).
87% Stage #1: 1-(3-bromophenyl)cyclopropane-1-carbonitrile With water; potassium hydroxide In ethylene glycol at 140℃; for 4h; Stage #2: With hydrogenchloride In water; ethylene glycol 1-(3-Bromophenyl)cyclopropanecarbonitrile (Reference compound 25-1, 5.0 g, 23 mmol) and ethylene glycol (20 mL) were added to a solution of potassium hydroxide (3.7 g, 66 mmol) in water (20 mL). The mixture was stirred at 140 °C for 4 hours. The reaction mixture was poured into a solution mixture of ice-water (100 mL) and 6 N hydrochloric acid (50 mL). The precipitated solid was separated by filtration and dried under reduced pressure to give the title reference compound (4.7 g) as a brown solid (yield 87 %). 1-(3-Bromophenyl)cyclopropanecarboxylic acid (Reference compound 26-1) [Show Image] 1H-NMR (400 MHz, CDCl3) δ 1.26 (dd, J = 7.2, 4.3 Hz, 2H), 1.68 (dd, J = 7.2, 4.3 Hz, 2H), 7.18 (t, J = 7.8 Hz, 1H), 7.28 (ddd, J = 7.8, 1.7, 1.0 Hz, 1H), 7.39 (ddd, J = 7.8, 1.7, 1.0 Hz, 1H), 7.49 (t, J = 1.7 Hz, 1H)
Stage #1: 1-(3-bromophenyl)cyclopropane-1-carbonitrile With sodium hydroxide; water In ethanol at 100℃; Stage #2: With hydrogenchloride In ethanol; water at 0℃; 10.2 Step 2: 1- (3-bromophenyl) cyclopropanecarboxylic acid; To a room temperature solution of 1- (3-BROMOPHENYL) cyclopropanecarbonitrile from Step 1 (12 g) in ethyl alcohol (100 ML) was added a solution of 50 mL of sodium hydroxide (25% NAOH in water W/W). The mixture was heated at 100 °C overnight. It was cooled to room temperature and poured into ice and 1N HCI, and extracted with dichloromethane (2 x 100 ML). The combined extracts were washed with brine, dried over magnesium sulfate and the solvent removed in vacuo to yield the title compound. H NMR (CD3COCD3) 8 10.80 (1H, bs), 7.60 (1H, s), 7.43 (1H, d), 7. 41 (1H, d), 7.29 (1H, t), 1. 58- 1.61 (2H, m), 1.23-1. 28 (2H, m).
With lithium hydroxide In water for 24h; Reflux;
With lithium hydroxide In water; ethylene glycol at 100℃; for 24h;
With water; lithium hydroxide for 24h; Reflux; General procedure: To a flask containing 1-aryl-1-cyanocyclopropane (S6) (6.6 mmol) was added a slurry of lithium hydroxide in water (4.0 M, 212 mmol). The flask was heated to reflux and stirred for 24 h. The reaction was cooled to room temperature, then 2 N HCI was added until pH < 1. The solution was extracted with ethyl acetate for three times. The combined ethyl acetate extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the desired 1-arylcyclopropanecarboxylic acid product, typically in sufficient purity to be carried forward to Pd-catalyzed reaction without further purification. The spectra of 4c6 and 4d7 have been reported in the literature.

  • 4
  • [ 31938-07-5 ]
  • [ 106-93-4 ]
  • [ 124276-83-1 ]
YieldReaction ConditionsOperation in experiment
95% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In water; at 20℃; 3-Bromophenylacetonitrile (5.0 g, 26 mmol) and 1,2-dibromoethane (6.6 mL, 77 mmol) were added to a solution of benzyltriethylammonium chloride (0.30 g, 1.3 mmol) in 50 % sodium hydroxide aqueous solution (20 mL), and the mixture was stirred at room temperature overnight. Ice-water (70 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (50 mL). The organic layer was washed with brine (30 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to give the title reference compound (5.4 g) as brown oil (yield 95 %). 1-(3-Bromophenyl)cyclopropanecarbonitrile (Reference compound 25-1) [Show Image] 1H-NMR (400 MHz, CDCl3) delta 1.40-1.43 (m, 2H), 1.74-1.77 (m, 2H), 7.20-7.28 (m, 2H), 7.40-7.44 (m, 2H)
  • 5
  • [ 124276-83-1 ]
  • [ 1454928-56-3 ]
  • [ 1454928-58-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 85℃; for 10h; Inert atmosphere; Sealed tube; 13 To a solution of l -(4-(tert-butyl)benzyl)-4-ethyl-3-(3-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)propyl)-lH-l,2,4-triazol-5(4H)-one (270 mg, 0.54 mmol) in DME (5 mL) and H20 (1.5 mL) was added l-(3-bromophenyl)cyclopropanecarbonitrile (143 mg, 0.64 mmol) and potassium carbonate (186 mg, 1.34 mmol). The resulting mixture was sparged with nitrogen gas for 10 minutes before tetrakis(triphenylphosphine)palladium (0) (20 mg) was added. The reaction vessel was then sealed and heated at 85 °C for 10 hrs. The reaction mixture was allowed to cool to RT and partitioned between EtOAc and water. The organic phase was separated, dried (MgSO i), filtered and the filtrate concentrated in vacuo. The residue thus obtained was purified using silica gel chromatography (0 to 70% EtOAc in hexanes) to afford l-(4'-(3-(l -(4-(te^butyl)ber^ biphenyl] -3 -yl)cyclopropanecarbonitrile.
  • 6
  • [ 124276-83-1 ]
  • [ 1533425-28-3 ]
  • [ 1533425-44-3 ]
YieldReaction ConditionsOperation in experiment
32% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos In toluene at 110℃; for 3h; Inert atmosphere; 59 1-{3-[5-[Bis(4-methoxybenzyl)amino]-1-(4-methoxybenzyl)-1H-[1,2,4]triazol-3-ylamino]phenyl}cyclopropanecarbonitrile In a 25 niL sealed tube, sodium 2-methylpropan-2-olate (62.7 mg, 653 μηιο, Eq: 1.20), bis(dibenzylideneacetone)palladium (31.3 mg, 54.4 μηιο, Eq: 0.1) and 2-di-tert-butyl(2',4',6'- triisopropylbiphenyl-2-yl)phosphine (23.1 mg, 54.4 μηιο, Eq: 0.1) were combined with toluene (5.00 mL) to give a dark brown suspension. N5,N5,l-tris(4-methoxybenzyl)-lH-l,2,4-triazole- 3,5-diamine (250 mg, 544 μηιο, Eq: 1.00) and l-(3-bromophenyl)cyclopropanecarbonitrile (121 mg, 544 μηιο, Eq: 1.00) were added. The reaction mixture was degassed with argon for 15 min, and then heated to 110°C for 3 hours. The reaction mixture was cooled and diluted with EtOAc (50 mL), washed with H20 (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgSC>4, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to give an off-white solid 105 mg (32%). MH+ 601.4
  • 7
  • [ 124276-83-1 ]
  • [ 1510823-43-4 ]
  • [ 1510822-90-8 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 1-(3-bromophenyl)cyclopropane-1-carbonitrile; (benzyloxy)chlorodiisopropylsilane With n-butyllithium In tetrahydrofuran at -100℃; for 0.5h; Inert atmosphere; Stage #2: In tetrahydrofuran at -100 - 20℃; for 2h; Inert atmosphere;
  • 8
  • [ 124276-83-1 ]
  • [ 1510823-43-4 ]
  • [ 145691-66-3 ]
  • C28H35NO3Si [ No CAS ]
  • C28H35NO3Si [ No CAS ]
  • C28H35NO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -100 °C / Inert atmosphere 1.2: 2 h / -100 - 20 °C / Inert atmosphere 2.1: palladium diacetate; N-acetylglycine; silver(I) acetate / 1,2-dichloro-ethane / 24 h / 90 °C / Inert atmosphere
  • 9
  • [ 124276-83-1 ]
  • C20H36O2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene / toluene / 5 h / 80 °C / Inert atmosphere; Glovebox 2: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 3: sodium tetrahydroborate / methanol / 1 h / 20 °C 4: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox
  • 10
  • [ 124276-83-1 ]
  • C25H34O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; potassium phosphate / toluene / 3 h / 100 °C / Inert atmosphere; Glovebox 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C 5: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox
  • 11
  • [ 124276-83-1 ]
  • C20H33NO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium phenoxide / toluene / 2 h / 100 °C / Inert atmosphere; Glovebox 4.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 °C 4.2: 0 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6.1: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox
  • 12
  • [ 124276-83-1 ]
  • C20H34O2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene / toluene / 5 h / 80 °C / Inert atmosphere; Glovebox 2: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 3: sodium tetrahydroborate / methanol / 1 h / 20 °C 4: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox 5: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S)-DTBM-SEGPHOS / tetrahydrofuran; cyclohexene / 24 h / 50 °C / Inert atmosphere; Glovebox
  • 13
  • [ 124276-83-1 ]
  • C25H32O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; potassium phosphate / toluene / 3 h / 100 °C / Inert atmosphere; Glovebox 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C 5: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox 6: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S)-DTBM-SEGPHOS / tetrahydrofuran; cyclohexene / 24 h / 50 °C / Inert atmosphere; Glovebox
  • 14
  • [ 124276-83-1 ]
  • C20H31NO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium phenoxide / toluene / 2 h / 100 °C / Inert atmosphere; Glovebox 4.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 °C 4.2: 0 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6.1: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox 7.1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S)-DTBM-SEGPHOS / tetrahydrofuran; cyclohexene / 24 h / 50 °C / Inert atmosphere; Glovebox
  • 15
  • [ 124276-83-1 ]
  • C16H24O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene / toluene / 5 h / 80 °C / Inert atmosphere; Glovebox 2: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C
  • 16
  • [ 124276-83-1 ]
  • (1-(3-((tert-butyldimethylsilyl)oxy)phenyl)cyclopropyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene / toluene / 5 h / 80 °C / Inert atmosphere; Glovebox 2: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 3: sodium tetrahydroborate / methanol / 1 h / 20 °C
  • 17
  • [ 124276-83-1 ]
  • C10H9BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 2h;
  • 18
  • [ 124276-83-1 ]
  • [ 886366-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: sodium tetrahydroborate / methanol / 1 h / 20 °C
  • 19
  • [ 124276-83-1 ]
  • ((1-(3-bromophenyl)cyclopropyl)methoxy)(tert-butyl)dimethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere
  • 20
  • [ 124276-83-1 ]
  • C27H38O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; potassium phosphate / toluene / 3 h / 100 °C / Inert atmosphere; Glovebox
  • 21
  • [ 124276-83-1 ]
  • tert-butyl 3'-(1-(hydroxymethyl)cyclopropyl)-[1,1'-biphenyl]-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; potassium phosphate / toluene / 3 h / 100 °C / Inert atmosphere; Glovebox 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C
  • 22
  • [ 124276-83-1 ]
  • C21H35NO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium phenoxide / toluene / 2 h / 100 °C / Inert atmosphere; Glovebox
  • 23
  • [ 124276-83-1 ]
  • C22H37NO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium phenoxide / toluene / 2 h / 100 °C / Inert atmosphere; Glovebox 4.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 °C 4.2: 0 °C
  • 24
  • [ 124276-83-1 ]
  • tert-butyl (3-(1-(hydroxymethyl)cyclopropyl)phenyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C 2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 3.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium phenoxide / toluene / 2 h / 100 °C / Inert atmosphere; Glovebox 4.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 °C 4.2: 0 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
  • 25
  • [ 124276-83-1 ]
  • sodium tert-butyldimethylsiloxide [ No CAS ]
  • C16H23NOSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 5h; Inert atmosphere; Glovebox;
  • 26
  • [ 110-91-8 ]
  • [ 124276-83-1 ]
  • C14H16N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 5h; Inert atmosphere; Glovebox;
  • 27
  • [ 124276-83-1 ]
  • [18F]-3-cyanocyclopropyldifluoromethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate / toluene / 15.5 h / 100 °C / Schlenk technique; Inert atmosphere 2.1: tetraethylammonium (F<SUP>18</SUP>)-flouride; tetraethylammonium bicarbonate; N-bromophthalimide / acetonitrile; chlorobenzene / 0.08 h / 100 °C / Schlenk technique; Inert atmosphere 2.2: 0.25 h / 100 °C
  • 28
  • [ 124276-83-1 ]
  • [ 450-95-3 ]
  • 3-(cyanocyclopropyl)phenylfluoroacetophenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate In toluene at 100℃; for 15.5h; Schlenk technique; Inert atmosphere;
  • 29
  • [ 124276-83-1 ]
  • [ 395-01-7 ]
  • 3-(cyanocyclopropyl)-1-difluoromethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: 1-(3-bromophenyl)cyclopropane-1-carbonitrile; 2,2-difluoro-1-phenylethanone With potassium phosphate monohydrate; bis(dibenzylideneacetone)-palladium(0); catacxium A In toluene at 100℃; for 30.3h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With water; potassium hydroxide In toluene at 100℃; for 2.7h; Schlenk technique; Inert atmosphere;
  • 30
  • [ 124276-83-1 ]
  • (1R,2R)-1-(3-bromophenyl)-2-(4-(methoxycarbonyl)phenyl)cyclopropane-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium hydroxide / water / 24 h / Reflux 2: palladium diacetate; sodium carbonate; silver carbonate; (S)-N-(1-(dimethylamino)-3-phenylpropan-2-yl)acetamide / 16 h / 80 °C / Sealed tube
  • 31
  • [ 124276-83-1 ]
  • C10H8BrFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium hydroxide; water / 16 h / 110 °C 2: hydrogen fluoride; sulfur tetrafluoride / dichloromethane / 36 h / 100 °C / Autoclave
  • 32
  • [ 124276-83-1 ]
  • 2-[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]acetic acid [ No CAS ]
  • 3-chloro-5-({1-[3-(1-cyanocyclopropyl)benzyl]-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; Ir[dF(CF3)ppy]2(4,4′-di-tert-butyl-2,2′-bipyridine)PF6; N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; Compounds 6-33; General Procedure General procedure: To 2 dram, stir-bar equipped vials, were added the aryl bromides (1.0 equiv). A stock solution of Ir[dF(CF3)ppy]2(dtbbpy)PF6 (1.0 mol%) and carboxylic acid 5 (1.1 equiv) in DMF (0.15 M with respect to carboxylic acid 5) was prepared, and to this stock solution was added TMG (1.1 equiv). The resulting stock solution was kept under a blanket of nitrogen. A separate solution of [Ni(dtbbpy)(H2O)4]Cl2 (10 mol%) in DMF (0.04 M) was prepared. The stock solution of Ir cat./acid/TMG was added to the aryl bromide monomers, followed by the Ni stock solution. The reaction mixtures were purged by blowing nitrogen over the top, sealed, and irradiated with blue LED (34 W LED Kessil lamps) for 24 h at room temperature. The reaction mixtures were diluted with EtOAc (3 mL) and H2O (4 mL). The organic layer was separated and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography with a solvent gradient from 0%EtOAc/hexanes to 100% EtOAc/hexanes to deliver the title compound.
  • 33
  • [ 124276-83-1 ]
  • C20H29BBrNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium hydroxide / water; ethylene glycol / 24 h / 100 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C 3: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H56BN3Si / tetrahydrofuran / 36 h / 60 °C / Schlenk technique
  • 34
  • [ 124276-83-1 ]
  • C14H18BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium hydroxide / water; ethylene glycol / 24 h / 100 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C
  • 35
  • C10H10BrNO [ No CAS ]
  • [ 124276-83-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2.1: (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine / N,N-dimethyl-formamide / 0.25 h / 20 °C / Glovebox 2.2: 12 h / 20 °C
  • 36
  • 1-bromo-3-(cyclopropylidenemethyl)benzene [ No CAS ]
  • [ 124276-83-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C 1.2: 1 h / 75 °C 2.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 3.1: (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine / N,N-dimethyl-formamide / 0.25 h / 20 °C / Glovebox 3.2: 12 h / 20 °C
  • 37
  • (Z)-2-(3-bromophenyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime [ No CAS ]
  • [ 124276-83-1 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: (Z)-2-(3-bromophenyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; for 0.25h; Glovebox; Stage #2: With lithium hexamethyldisilazane In N,N-dimethyl-formamide at 20℃; for 12h; General procedure IV for the synthesis of cyclopropane derivatives General procedure: To a 4 ml screwed-capped vial was added oxime ester 1 (0.2 mmol), NiCl2 glyme (4 mg, 0.02 mmol), Ligand (5 mg, 0.02 mmol), DMF (0.2 ml) in Glove box. Theresulting mixture was stirred for 15min at room temperature. To the solution was addedLiHMDS (0.4ml, 1.0 M, 0.4 mmol). The vial was removed from Glove box and stirredat room temperature for 12h. After this time, the reaction mixture was quenched withsaturated ammonia chloride (1N), and diluted with ethyl acetate. The organic layer wasseparated and dried over anhydrous Na2SO4, filtered and removed under vacuum. Thecorresponding product was obtained by flash chromatography.
  • 38
  • [ 3132-99-8 ]
  • [ 124276-83-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 80 °C 1.2: 5 h / Reflux 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C 2.2: 1 h / 75 °C 3.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 4.1: (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine / N,N-dimethyl-formamide / 0.25 h / 20 °C / Glovebox 4.2: 12 h / 20 °C
YieldReaction ConditionsOperation in experiment
63.6% Stage #1: With sodium hydride In N,N-dimethyl acetamide; mineral oil at -15 - -10℃; for 0.25h; Inert atmosphere; Stage #2: In N,N-dimethyl acetamide; mineral oil at -10 - 20℃; for 1h; 1-11 Example 1-1 General procedure: -15°C and under N2 protection,2.5eq of 60% sodium hydride (9.25g, 231.25mmol)Add to 120ml of dimethylacetamide,Dissolve 1.0eq of phenylacetonitrile in 60ml of dimethylacetamide,and slowly added dropwise into the system,At the same time, control the temperature not to exceed -10°C,It was then kept stirring for 15 minutes at -15°C.1.1 eq of 1-bromo-2-chloroethane (14.59 g, 101.75 mmol)Dissolved in 60ml of dimethylacetamide,and slowly added dropwise into the system,At the same time control the temperature not to exceed -10°C.After the addition was completed, the temperature was naturally raised to room temperature and stirred for 1 hour.After the reaction is completed, add water to quench and extract with ethyl acetate:petroleum ether=1:10, combine the organic phases, dry with anhydrous sodium sulfate, concentrate, and purify the crude product by silica gel column chromatography, the eluent is ethyl acetate:petroleum ether = 1:10,The solvent is concentrated to obtain the target arylcyclopropane compound.In the present embodiment, phenylacetonitrile is 3-fluorophenylacetonitrile and adopts the method of embodiment 1-1,The compound 1-(3-fluorophenyl)cyclopropane-1-carbonitrile (14.46g) was obtained with a yield of 97%
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 124276-83-1 ]

Aryls

Chemical Structure| 124276-67-1

[ 124276-67-1 ]

1-(4-Bromophenyl)cyclopropanecarbonitrile

Similarity: 0.97

Chemical Structure| 1360551-88-7

[ 1360551-88-7 ]

2-(4-Bromophenyl)-2-cyclopropylpropanenitrile

Similarity: 0.94

Chemical Structure| 1082600-86-9

[ 1082600-86-9 ]

2-(4-Bromophenyl)-2-cyclopropylacetonitrile

Similarity: 0.94

Chemical Structure| 51632-12-3

[ 51632-12-3 ]

2-(4-Bromophenyl)-3-methylbutanenitrile

Similarity: 0.94

Chemical Structure| 29786-38-7

[ 29786-38-7 ]

1-(3-Bromophenyl)cyclobutane-1-carbonitrile

Similarity: 0.92

Bromides

Chemical Structure| 124276-67-1

[ 124276-67-1 ]

1-(4-Bromophenyl)cyclopropanecarbonitrile

Similarity: 0.97

Chemical Structure| 1360551-88-7

[ 1360551-88-7 ]

2-(4-Bromophenyl)-2-cyclopropylpropanenitrile

Similarity: 0.94

Chemical Structure| 1082600-86-9

[ 1082600-86-9 ]

2-(4-Bromophenyl)-2-cyclopropylacetonitrile

Similarity: 0.94

Chemical Structure| 51632-12-3

[ 51632-12-3 ]

2-(4-Bromophenyl)-3-methylbutanenitrile

Similarity: 0.94

Chemical Structure| 29786-38-7

[ 29786-38-7 ]

1-(3-Bromophenyl)cyclobutane-1-carbonitrile

Similarity: 0.92

Nitriles

Chemical Structure| 124276-67-1

[ 124276-67-1 ]

1-(4-Bromophenyl)cyclopropanecarbonitrile

Similarity: 0.97

Chemical Structure| 1360551-88-7

[ 1360551-88-7 ]

2-(4-Bromophenyl)-2-cyclopropylpropanenitrile

Similarity: 0.94

Chemical Structure| 1082600-86-9

[ 1082600-86-9 ]

2-(4-Bromophenyl)-2-cyclopropylacetonitrile

Similarity: 0.94

Chemical Structure| 51632-12-3

[ 51632-12-3 ]

2-(4-Bromophenyl)-3-methylbutanenitrile

Similarity: 0.94

Chemical Structure| 29786-38-7

[ 29786-38-7 ]

1-(3-Bromophenyl)cyclobutane-1-carbonitrile

Similarity: 0.92