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Chemical Structure| 850568-67-1 Chemical Structure| 850568-67-1
Chemical Structure| 850568-67-1

2-(4-Boronophenyl)-2-methylpropanenitrile

CAS No.: 850568-67-1

4.5 *For Research Use Only !

Cat. No.: A248969 Purity: 98%

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Product Details of [ 850568-67-1 ]

CAS No. :850568-67-1
Formula : C10H12BNO2
M.W : 189.02
SMILES Code : C(#N)C(C)(C)C1=CC=C(C=C1)B(O)O
MDL No. :MFCD06659832
InChI Key :BNXBFDTWYHAEIR-UHFFFAOYSA-N
Pubchem ID :44119324

Safety of [ 850568-67-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 850568-67-1 ]

* 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 [ 850568-67-1 ]

[ 850568-67-1 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 930-68-7 ]
  • [ 850568-67-1 ]
  • [ 3886-70-2 ]
  • [ 1157580-33-0 ]
YieldReaction ConditionsOperation in experiment
General procedure M.To a solution of cycloalkenone (400 mumol) in 400 muL DME were added boronic acid (480 mumol, 1.2 eq.), (COD)Rh(l,4-dihydroquinone)BF4 (1 mol%) in 100 muL DME, and LiOH (4 mol%) in 600 muL water. After shaking the mixture overnight at 50 0C, the solvent was removed in vacuo. The crude intermediate ketone was dissolved in DCE containing acetic acid (1.2 eq.). (+)-(/R)-l-naphthalen-l-yl-ethyIamine (1 eq.) in DCE was added <n="136"/>followed by NaBH(OAc)3 (1.2 eq.) The mixture was shaken overnight at r. t., filtered and the solvents were removed in vacuo. The residue was redissolved in 750 mul_ DMSO and purified by HPLC.Example 214: 2-Methyl-2-{4-[3-((beta)-l-naphthalen-l-yl-ethylamino)-cyclohexyl]- phenyl>-propionitrile (compound 1236/1237)General procedure M was followed using 4-(2-cyanopropan-2-yl) phenylboronic acid and 2-cyclohexen-l-one. The title compounds were purified by chromatography on 20 g silica gel in a gradient from 0 to 60% EtOAc in n-heptane, flow rate 30 mL/min. Compound 1236 (1 isomer, less polar, RT ~ 11 min): 13C NMR (75 MHz, DMSO) delta 146.84, 142.38, 138.59, 133.47, 130.84, 128.60, 127.05, 126.42, 125.62, 125.54, 125.15, 124.80, 124.69, 123.04, 122.94, 50.88, 49.99, 38.75, 36.56, 36.17, 33.17, 28.94, 28.26, 24.52, 20.25. Compound 1237 (1 isomer, more polar, RT ~ 13 min): 13C NMR (75 MHz, DMSO) delta 146.76, 142.14, 138.61, 133.39, 130.84, 128.55, 127.18, 126.39, 125.62, 125.50, 125.10, 124.85, 124.66, 122.92, 122.80, 50.11, 49.30, 36.44, 36.28, 36.15, 33.36, 30.74, 28.24, 24.40, 20.50.
  • 2
  • [ 850568-67-1 ]
  • [ 1321612-96-7 ]
  • [ 1321606-29-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water;Reflux; General Procedure 4 (GP4): Suzuki CouplingThe 4-chloropyrimidine (1.0 eq.) is dissolved in DME/water (20: 1 v/v), boronic acid (1.3 eq.), K2CO3 (2.0 eq.) and Pd(PPh3)4 (0.2 eq.) are added and the reaction mixture is stirred for 4 h under reflux. In case the conversion of the starting material is not complete, additional amounts of boronic acid and Pd-catalyst are added and the reaction is run over night under reflux. After cooling to RT water is added. The precipitate is filtered off. In cases where the product is not precipitated it is extracted with diethylether, the organic phase is dried, filtered off, and the solvent removed under reduced pressure. The obtained product can either be used without further purification or is purified by chromatography.
  • 3
  • [ 1780-31-0 ]
  • [ 850568-67-1 ]
  • [ 1341200-65-4 ]
  • 4
  • [ 1780-31-0 ]
  • [ 850568-67-1 ]
  • [ 1341200-41-6 ]
  • 5
  • [ 850568-67-1 ]
  • [ 1350455-42-3 ]
  • [ 1350455-52-5 ]
  • 6
  • [ 121-43-7 ]
  • [ 101184-73-0 ]
  • [ 850568-67-1 ]
  • 7
  • [ 850568-67-1 ]
  • [ 139585-70-9 ]
  • [ 1431616-21-5 ]
  • 8
  • [ 850568-67-1 ]
  • [ 1454654-37-5 ]
  • 9
  • [ 850568-67-1 ]
  • [ 1454654-35-3 ]
  • 10
  • [ 850568-67-1 ]
  • [ 33332-28-4 ]
  • [ 1454654-36-4 ]
YieldReaction ConditionsOperation in experiment
69.28% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; toluene; at 130℃; for 1h;Microwave irradiation; 16.1 2-[4-(6-amino- razin-2-yl)-phenyl]-2-methyl-propionitrile To a solution of 2-amino-6-chloro-pyrazine (0.5 g, 3.86 mmol) in toluene / ethanol (9:1 , 10 ml), <strong>[850568-67-1]4-(1-cyano-1-methylethyl)phenyl boronic acid</strong> (0.8 g, 4.24 mmol), tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.11 mmol) and cesium carbonate (2.5 g, 7.72 mmol) are added, degassed briefly and irradiated in microwave at 130 °C for an hour. The reaction mixture is passed through celite, washed with dichloromethane/methanol (1 :1 , 25 ml), the filtrate is concentrated and purified by silica column using (230-400) mesh to get the product as yellow solid (0.63 g, 69.28 percent); TLC: chloroform/methanol (9.5/0.5) Rf- 0.2; 1H NMR: 400 MHz, DMSO-d6: delta [ppm] 8.29 (s, 1 H), 8.03 (dd, J = 1.92, 6.68 Hz, 2H), 7.85 (s, 1 H), 7.61 (dd, J = 1.88, 6.68 Hz, 2H), 6.54 (br s, 2H), 1.70 (s, 6H); LCMS: Mass found (M+, 239.3) Method: A-0.1percent TFA in H20, B-0.1percent TFA in ACN: Flow - 2.0 ml/min. Column: XBridge C8 (50 X 4. 6mm, 3.5 pm), +ve mode Rt (min): 3.06 area percent -93.86 (Max), 99.39 (254 nm).
  • 11
  • [ 850568-67-1 ]
  • [ 1442116-57-5 ]
  • [ 1442121-23-4 ]
YieldReaction ConditionsOperation in experiment
67 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; for 0.333333h;Reflux; General procedure: 80 mg of the aryl bromide prepared in Example 316 together with 32 mg of (5-chloropyridin-2-yl)boronic acid was first placed in 1 ml tetrahydrofuran, treated with 17.3 mg of 1,1'-bis(diphenylphosphino)ferrocenodichloropalladium(II) and 0.17 ml of 1M potassium carbonate solution and heated in the microwave for 10 minutes at 120 C. (100 watts). After fresh addition of 11 mg of (5-chloropyridin-2-yl)boronic acid and 17.3 mg of the palladium(II) catalyst, the reaction mixture was again heated in the microwave for 10 minutes at 120 C. (100 watts) until complete conversion. The reaction mixture was concentrated. After HPLC purification, this yielded 15 mg of the title compound. Analogously to Example 317, 67 mg of the title compound was obtained from 100 mg of 54 and 55 mg of <strong>[850568-67-1][4-(1-cyano-1-methylethyl)phenyl]boronic acid</strong> under reflux. 1H-NMR (400 MHz, DMSO-d6): delta [ppm], 1.28 (2H), 1.36-1.65 (2H), 1.72 (6H), 2.24-2.40 (1H), 2.53 (3H), 2.70-3.14 (2H), 3.28 (3H), 3.36-3.43 (2H), 3.43-3.49 (2H), 3.54-3.77 (1H), 4.36 (3H), 7.18 (1H), 7.38-7.50 (3H), 7.62 (2H), 7.75 (4H), 8.15 (1H), 8.52 (1H).
  • 12
  • [ 850568-67-1 ]
  • 3-bromo-1-tert-butyloxycarbonyl-2-indolyl diphenyl phosphate [ No CAS ]
  • 1-tert-butyloxycarbonyl-3-[4-(2-cyanoprop-2-yl)phenyl]-2-indolyl diphenyl phosphate [ No CAS ]
  • 13
  • [ 850568-67-1 ]
  • 3-(1H-benzo[d]imidazol-2-yl)-5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole [ No CAS ]
  • 2-(4-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)phenyl)-2-methylpropanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
7 mg With palladium diacetate; sodium carbonate; triphenylphosphine; In tetrahydrofuran;Reflux; 3-(1H-benzo[d] imidazol-2-yl)-5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 9 (20 mg, 0.050 mmol), [4-(1cyano-1-methylethyl)phenyl]boronic acid (10 mg, 0.074053 mmol) and triphenylphosphine (2 mg, 0.007 mmol) were dissolved in a mixture of THF (6 mL) and aq. 1M Na2CO3 (10 mg, 0.094 mmol). Palladium acetate (1 mg, 0.004 mmol) was added and the solution was heated overnight at reflux. After cooling to room temperature, and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (25 mL) and washed with water (20 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (25 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound (7 mg). 1H NMR (400 MHz, CDCl3): delta 8.79 (s, 1H), 7.80 (bs, 1H), 7.75 (m, 2H), 7.70 (m, 1H), 7.64 (m, 1H), 7.53-7.48 (m, 3H), 7.25-7.22 (m, 2H), 5.76 (d, 1H, J = 8.4 Hz), 4.06 (m, 1H), 3.77 (m, 1H), 2.55 (m, 1H), 2.10 (m, 2H), 1.73 (m, 3H), 1.72 (s, 6H).
  • 14
  • [ 850568-67-1 ]
  • [ 100-59-4 ]
  • [ 1122-91-4 ]
  • 1-[4'-(2-cyanoprop-2-yl)biphenyl-4-yl]-1-phenylmethanol [ No CAS ]
  • 15
  • [ 850568-67-1 ]
  • diethyl 2-bromocyclobuten-1-yl phosphate [ No CAS ]
  • diethyl 2-[4-(2-cyanoprop-2-yl)phenyl]cyclobuten-1-yl phosphate [ No CAS ]
  • 16
  • [ 850568-67-1 ]
  • tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-6-cyano-3-iodo-1H-indazole-1-carboxylate [ No CAS ]
  • 3-(4-(2-cyanopropan-2-yl)phenyl)-5-(2-fluoro-6-methyl-4-((methylamino)methyl)phenyl)-1H-indazole-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A vial equipped with a magnetic stir bar was charged with tert-butyl 5-(4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-6-cyano-3-iodo-1H-indazole-1-carboxylate (12.0 mg, 0.019 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.58 mg, 0.025 mmol), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (XPhos Pd G2, 2.3 mg, 3 mumol) and potassium phosphate (8 mg, 0.039 mmol). The vial was sealed, evacuated and backfilled with nitrogen (this process was repeated a total of three times). Then 1,4-dioxane (2.00 ml) was added followed by water (200.0 mul). The reaction mixture was heated to 80 C. for 2 h. After cooling to room temperature, the reaction mixture was concentrated under vacuum. The residue was treated with CH2Cl2 (1 mL) followed by TFA (1 mL). The mixture was stirred at room temperature for 15 min, and then concentrated under vacuum. The residue was purified using prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min) to afford the desired product. LCMS calculated C22H22FN6 (M+H)+: m/z=389.2; found: 389.2.
  • 17
  • [ 850568-67-1 ]
  • ethyl 4-bromo-6-fluoroquinoline-3-carboxylate [ No CAS ]
  • ethyl 4-(4-(2-cyanopropan-2-yl)phenyl)-6-fluoroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.9% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 95℃; for 2h;Inert atmosphere; High pressure; In a 2-neck flask was placed ethyl 4-bromo-6-fluoroquinoline-3-carboxylate (894 mg, 3 mmol), <strong>[850568-67-1](4-(2-cyanopropan-2-yl)phenyl)boronic acid</strong> (652 mg, 3.45 mmol), PdCl2(dppf)-CH2Cl2 adduct (245 mg, 0.30 mmol), and K2C03 (954 mg, 6.90 mmol). The air was removed and re-filled with N2 (2-3 times). Then added a mixture of 1,4-Dioxane (6 ml) and Water (3 ml) was added and stirred at 95 C (pre -heated) for 2 h. The organic layer was separated and the aqueous layer was extracted with EtOAc (5 mL x 2). The combined organic was dried (Na2S04) and filtered. After removal of solvent, the product was purified by silica gel chromatography using 20-50% EtOAc/hexane as the eluent to give ethyl 4-(4-(2-cyanopropan-2-yl)phenyl)-6-fluoroquinoline-3- carboxylate (390 mg, 1.076 mmol, 35.9 % yield). LC-MS (Method 1): tR= 3.66 min, m/z (M+H)+= 363.
  • 18
  • [ 850568-67-1 ]
  • 4-(4-(2-cyanopropan-2-yl)phenyl)-6-fluoroquinoline-3-carboxylic acid [ No CAS ]
  • 19
  • [ 850568-67-1 ]
  • 2-(4-(6-fluoro-3-(4-(methylsulfonyl)piperidine-1-carbonyl)quinolin-4-yl)phenyl)-2-methylpropanenitrile trifluoroacetate [ No CAS ]
 

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