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[ CAS No. 935685-88-4 ]

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Chemical Structure| 935685-88-4
Chemical Structure| 935685-88-4
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Product Details of [ 935685-88-4 ]

CAS No. :935685-88-4 MDL No. :MFCD11521351
Formula : C13H15BFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :247.07 g/mol Pubchem ID :-
Synonyms :

Safety of [ 935685-88-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 935685-88-4 ]

  • Downstream synthetic route of [ 935685-88-4 ]

[ 935685-88-4 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 73183-34-3 ]
  • [ 179898-34-1 ]
  • [ 935685-88-4 ]
YieldReaction ConditionsOperation in experiment
100% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere; 3-Bromo-5-fluoro benzonitrile (30 g, 150 mmol), bis(pinacolato)diborane (41.9 g,0.lSmol) and potassium acetate (44.2 g, 0.45mo1) were combined in 1,4-dioxane(300 mL) and degassed with N2 for 10 mins. [1,1-Bis(dipheny[phosphino)ferrocene] pa[[adium(II) dichloride (5.5 g, 7.5 mmo[) wasadded and the mixture degassed with N2 for a further 10 mm before heating at 100C under an atmosphere of nitrogen for 18 h. The mixture was filtered throughCelite and the solids washed with ethyl acetate. The filtrate was washed withbrine, the organic phase separated, dried over MgSO4, filtered and concentratedunder reduced pressure. The crude material was purified by filtration through a silica plug, eluting with EtOAc, and the resultant filtrate concentrated under reduced pressure to afford 43.7 g (quantitative yield assumed, 84 % purity) of the title compound as brown oil1H NMR (500MHz, DMSO-d6): 6 [ppm] 1.31 (5, 12H), 7.65-7.72 (m, 1H), 7.79-7.83 (m, 1H), 8.00 (ddd, J = 8.8, 2.7, 1.4 Hz, 1H).LCMS (Analytical Method A) Rt = 0.91 mm.
97% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 2h; Intermediate T5: 3-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile A mixture of <strong>[179898-34-1]3-bromo-5-fluorobenzonitrile</strong> (0.300 g, 1.5 mmol), bis(pinacolato) diboron (0.762 g, 3 mmol), KOAc (0.589 g, 6.0 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.110 g, 0.15 mmol) in dioxane (15 mL) was stirred at 90 C. for 2 h. The solvent was removed and the residue was purified by flash chromatography on Biotage silica 50 g cartridge (cyclohexane to cyclohexane:EtOAc=70:30) to afford title compound (0.360 g, 1.46 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.98-8.03 (m, 1H), 7.81-7.85 (m, 1H), 7.68-7.73 (M, 1H), 1.33 (s, 12H).
92% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; at 90℃;Inert atmosphere; Example 5A 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenecarbonitrile Under argon, 3.60 g (18.0 mmol) of <strong>[179898-34-1]3-bromo-5-fluorobenzenecarbonitrile</strong>, 5.03 g (19.8 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane and 5.30 g (54.0 mmol) of potassium acetate are provided in 72 ml of degassed 1,4-dioxane/DMSO (10/1), and 441 mg (0.54 mmol) of 1,1'-bis(diphenylphosphine)ferrocenedichloropalladium(II)/dichloromethane complex are added. The mixture is stirred at 90 C. overnight. Water is subsequently added, the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 4.48 g (92% of theory) of the title compound are obtained. 1H-NMR (400 MHz, DMSO-d6): delta=8.01 (ddd, 1H), 7.82 (s, 1H), 7.70 (ddd, 1H), 1.32 (s, 12H). GC-MS (Method 11): Rt=4.94 min; MS (EIpos): m/z=247 [M]+.
92% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; dimethyl sulfoxide; at 90℃;Inert atmosphere; Under argon, 3.60 g (18.0 mmol) of <strong>[179898-34-1]3-bromo-5-fluorobenzenecarbonitrile</strong>, 5.03 g (19.8 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane and 5.30 g (54.0 mmol) of potassium acetate are provided in 72 ml of degassed 1,4-dioxane/DMSO (10/1), and 441 mg (0.54 mmol) of 1,1'-bis(diphenylphosphine)ferrocenedichloropalladium(II)/dichloromethane complex are added. The mixture is stirred at 90 C. overnight. Water is subsequently added, the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 4.48 g (92% of theory) of the title compound are obtained.1H-NMR (400 MHz, DMSO-d6): delta=8.01 (ddd, 1H), 7.82 (s, 1H), 7.70 (ddd, 1H), 1.32 (s, 12H).GC-MS (Method 11): Rt=4.94 min; MS (EIpos): m/z=247 [M]+.
92% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; dimethyl sulfoxide; at 90℃;Inert atmosphere; Example 21A 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenecarbonitrile Under argon, 3.60 g (18.0 mmol) of <strong>[179898-34-1]3-bromo-5-fluorobenzenecarbonitrile</strong>, 5.03 g (19.8 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane and 5.30 g (54.0 mmol) of potassium acetate are provided in 72 ml of degassed 1,4-dioxane/DMSO (10/1), and 441 mg (0.54 mmol) of 1,1'-bis(diphenylphosphine)ferrocenedichloropalladium(II)/dichloromethane complex are added. The mixture is stirred at 90 C. overnight. Water is subsequently added, the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are concentrated. The crude product is purified by flash chromatography (mobile phase:cyclohexane/ethyl acetate 10:1). 4.48 g (92% of theory) of the title compound are obtained. 1H-NMR (400 MHz, DMSO-d6): delta=8.01 (ddd, 1H), 7.82 (s, 1H), 7.70 (ddd, 1H), 1.32 (s, 12H). GC-MS (Method 11): Rt=4.94 min; MS (EIpos): m/z=247 [M]+.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 4h; Example 1; 3-fluoro-5-{5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridin-2-yl}benzonitrile; Step 1: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; 3-Bromo-5-fluorobenzonitrile (30.0 mmol, 9.23 g), bis(pinacolato)diboron (30.0 mmol, 7.62 g), PdCl2(dppf)2 (1:1 complex with dichloromethane, 1.2 mmol, 980 mg), and potassium acetate (105 mmol, 10.3 g) were combined in deoxygenated dioxane (150 mL) and heated at 80 C. for 4 hrs, at which time the reaction was determined to be complete by GC/MS analysis. The reaction was cooled to room temperature, and poured in to a separatory funnel containing EtOAc (300 mL) and water (200 mL). The aqueous layer was back extracted with EtOAc (75 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was carried on to the next step with out further purification or characterization.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 100 - 110℃; for 6h; Intermediate 20. 3-fluoro-5-(4 A5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzonitrile; [0186] To a mixture of <strong>[179898-34-1]3-bromo-5-fluorobenzonitrile</strong> (100 g, 0.5 mol, Oakwood Products, Inc., West Columbia, SC, USA), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (280 g, 1.4 mol), potassium acetate (135 g, 1.1 mol) in DMF (1200 mL) was added Pd(dppf)Cl2 (21 g, 28 mmol). The mixture was heated at 100-110 C for 6 h. DMF was evaporated and the residue was suspended in water and extracted with EtOAc (3X). The combined EtOAc layers were dried over Na2SO4 and evaporated. The residue was purified by column chromatography (PE : EA = 10 : 1 v/v) to give 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzonitrile (20) (190 g in 60% purity).[0187] 1HNMR (CDCl3, 400MHz): delta 7.84 (s, 1H), 7.68 (d, 1H), 7.38 (m, 1H), 1.32 (s, 12H).

  • 2
  • [ 935685-88-4 ]
  • [ 329204-13-9 ]
  • [ 935685-90-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,2-dimethoxyethane; water at 20 - 80℃; 1.2 Step 2: 3-fluoro-5-{5-[(2-methyl-3-thiazol-4-yl)ethynyl]pyridin-2-yl}benzonitrile; 2-chloro-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine (30 mmol, 7.02 g) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (30 mmol, crude material, above procedure), dichlorobis(triphenylphosphine)palladium(II) (1.5 mmol, 1.05 g), and potassium carbonate (120 mmol, 16.6 g) were added to deoxygenated DME:water (1:1, 300 mL) at room temperature. The reaction was warmed to 80° C. and stirred overnight under nitrogen, then partitioned in a separatoly funnel with EtOAc (500 mL) and water (300 mL). The organic layer was washed with one additional portion of water (100 mL) and the combined aqueous layers back extracted with EtOAc (100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was chromatographed on SiO2, eluting with 30% EtOAc in hexanes, to afford the title compound as a tan solid. 1H-NMR (CDCl3, 500 MHz) δ 8.89 (m, 1H), 8.17 (dd, 1H), 8.04 (m, 1H), 7.98 (dd, 1H), 7.75 (d, 1H), 7.50 (s, 1H), 7.42 (m, 1H), 2.79 (s, 3H). MS (ESI) 320.0 (M+H+).
  • 3
  • [ 935685-88-4 ]
  • [ 850349-12-1 ]
  • [ 1242846-67-8 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere; 64 Intermediate 21. t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate (21); [0188] To solution of tert-butyl 2-(2-bromo-4-formylphenoxy)acetate (1) (120 g, 0.38 mol) in dioxane / H2O (4:1, 700 mL) was added 3-fluoro-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (20) (158 g in 60% purity, 0.38 mol), Na2CO3 (81 g, 0.76 mol) and Pd(PPh3)4 (22 g, 19 mmol) under N2. The mixture was stirred at 80 °C for 3 h. After cooling to room temperature, the mixture was concentrated in vacuo and purified by column chromatography (PE : EA = 10 : 1 v/v) to give 90 g of t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate (21) (90 g, 67%).
  • 4
  • [ 935685-88-4 ]
  • [ 1245515-86-9 ]
  • [ 1245509-34-5 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In 1,4-dioxane at 100℃; for 1.5h; Microwave irradiation; Inert atmosphere; 38 A mixture of compound 13f (20 mg, 0.053 mmol), 3-fluoro-5-(4 ,4,5,5- tetramethyl-l,3-dioxolan-2-yl) benzonitrile (20 mg, 0.08 mmol), Cs2CO3 (2 M, 0.300 mL), and Pd(PPh3)2Cl2 (5 mg) in 1,4-dioxane (1 mL) under Ar2 was stirred at 1000C for 90 minutes. The reaction mixture was concentrated in vacuum, the residue was purified by preparative TLC and HPLC to give compound 8 (1.85 mg, 8%). 1H-NMR (400 Hz CD3OD): δ 7.85-8.00 (m, IH), 7.70-7.85 (m, 3H), 7.50-7.65 (m, IH), 7.40-7.50 (m, IH), 3.23-3.45 (m, 6H), 3.15-3.25 (m, IH), 2.95-3.05 (m, 2H), 2.00-2.20 (m, 2H), 1.64- 1.95 (m, 2H), 1.30-1.55 (m, 4H); ESI MS: m/z=421 [M+H]+.
  • 5
  • [ 935685-88-4 ]
  • [ 1245509-58-3 ]
  • [ 1245510-54-6 ]
YieldReaction ConditionsOperation in experiment
20% With caesium carbonate In 1,4-dioxane at 120℃; for 0.25h; Microwave irradiation; Inert atmosphere; 153 Pd(PPh3)2Cl2 (5 mg) in a 10 mL of flask under a nitrogen atmosphere was treated sequentially with compound 1-6 (25 mg, 0.06 mmol) in 1,4-dioxane (2 mL), Cs2CO3 (2 N, 0.09 mL, 0.18 mmol) and compound 192A (31.5 mg, 0.12 mmol). The mixture was heated at 120 0C in a CEM microwave reactor under a nitrogen atmosphere for 15 min. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC (CH2Cl2: MeOH = 10:1) and preparative HPLC to give compound 192 (5.6 mg, 20%) as a white solid. LC-MS tR = 0.958 min in 2 min chromatography, MS (ESI) m/z 433.1 [M+H]+; 1H NMR (CD3OD 400MH): δ 7.83 (s, IH), 7.70-7.77 (m, IH), 7.59 (m, IH), 7.50 (m, IH), 7.43 (m, IH), 7.27 (s, IH), 3.26 (s, 3H), 3.13 (m, 3H), 3.05 (s, 3H), 1.81-2.04 (m, 3H), 1.64 (m, IH), 1.25-1.46 (m, 4H)
  • 6
  • [ 75-52-5 ]
  • [ 935685-88-4 ]
  • [ 141-97-9 ]
  • [ 1122-91-4 ]
  • [ 100-46-9 ]
  • [ 1318763-80-2 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: nitromethane; ethyl acetoacetate; 4-bromo-benzaldehyde; benzylamine With bis-triphenylphosphine-palladium(II) chloride at 80 - 85℃; for 4h; Inert atmosphere; Neat (no solvent); Stage #2: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenecarbonitrile With potassium carbonate In 1,4-dioxane; water at 80 - 85℃; for 5h; Inert atmosphere;
  • 7
  • [ 3132-99-8 ]
  • [ 90-15-3 ]
  • [ 935685-88-4 ]
  • [ 109-77-3 ]
  • [ 1343978-35-7 ]
YieldReaction ConditionsOperation in experiment
93% With pyrrolidine; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 0 - 70℃; Preparation of 4-biaryl substituted 2-amino benzochromenes (5) General procedure: A mixture of 1-naphthol 1 (10 mmol), malononitrile 2 (10 mmol), bromo aldehyde 3 (10 mmol) and an aryl boronic acid (12.0 mmol) in dioxane (5 mL) was cooled to 0-5 °C. To this was added (PPh3)2PdCl2 (0.002 mmol) and pyrrolidine (5 mmol) maintaining the temperature at 0-5 °C. The mixture was stirred for 30 minutes, warmed to room temperature and then heated to 70 °C. The stirring continued according to the duration indicted in Table 2 (progress of the reaction was monitored by TLC). Upon completion of the reaction, the mixture was cooled, diluted with water (15 mL) and extracted with ethyl acetate (2x5 mL). The combined organic layers were collected, washed with aqueous brine (3 x 5 mL), dried over anhydrous magnesium sulphate and concentrated under low vacuum. The crude material was purified by silica gel chromatography using 0-25% ethyl acetate/hexane.
93% With palladium 10% on activated carbon; tetrabutylammomium bromide; sodium carbonate In water; N,N-dimethyl-formamide at 5 - 60℃; for 2.5h; Inert atmosphere; Sonication; 2.2.1. General Procedure General procedure: A mixture of 1-naphthol 1 (1mmol), malononitrile 2 (1 mmol), bromo aldehyde 3 (1 mmol), aryl boronic acid 4 (1.2mmol) in 5:1 DMF/H2O (5 mL) was cooled to 5-10 °C. To this was added 10%Pd/C (1.5 mol%), Na2CO3 (3 mmol) and TBAB (1 mmol) maintaining the temperature at 5-10 °C. The mixture was stirred for 30 minutes under ultrasound irradiation, warmed to room temperature and then heated to 55-60 °C and stirred under ultrasound irradiation at this temperature. The temperature of the bath was maintained at 55-60 °C by adding appropriate volume of cold water time to time in case if the temperature was increased. The stirring continued according to the duration indicated in Table 2 (progress of the reaction was monitored by TLC). Upon completion of the reaction, the mixture was cooled, filtered to remove the catalyst, diluted with water (15 mL) and extracted with ethyl acetate (2*5 mL). The combined organic layers were collected, washed with aqueous brine (3 * 5 mL), dried over anhydrous Na2SO4 and concentrated under low vacuum. The crude material was purified by silica gel chromatography using 0-25% ethyl acetate/hexane.
YieldReaction ConditionsOperation in experiment
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; for 24h; 7 Synthesis of Intermediate (E) General procedure: 15.0 g (75.0 mmol) of 3-bromo-2-fluorobenzonitrile, 22.9 g (90.0 mmol) of bis(pinacolato)diboron, 3.06 g (3.75 mmol) of PdCl2(dppf).CH2Cl2, and 22.1 g (225 mmol) of potassium acetate were dissolved in 250 ml of DMF, and the resulting solution was stirred at a temperature of 100° C. for 24 hours. After completion of the reaction, the resulting reaction solution was cooled to room temperature and filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 12.4 g (yield: 67%) of a desired compound, Intermediate (E). LC-Mass (cald: 247.12 g/mol, found: M+1=248 g/mol).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 4h; Inert atmosphere; 16 15. Preparation of 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile General procedure: 3-bromo-2-fluorobenzonitrile (500 mg, 2.5 mmol), bis(pinacolato)borate (950 mg, 3.5 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium chloride (185 mg, 0.25 mmol) and potassium acetate (491 mg, 5.0 mmol) were mixed in 1,4-dioxane (6 mL). The nitrogen was charged to replace three times by evacuation. The mixture solution was reacted at a temperature of 100° C. for 4 hrs. After the reaction was completed, the reaction mixture was filtered. The filtrate was concentrated, and the residue was separated by a rapid silica gel column [eluent:EtOAc:PE=0-20%] to obtain 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (450 mg, 73%). (0224) 1H NMR (400 MHz, CDCl3) δ 7.98 (ddd, J=7.5, 5.6, 1.9 Hz, 1H), 7.71 (ddd, J=7.9, 6.3, 1.9 Hz, 1H), 7.26 (d, J=7.6 Hz, 1H), 1.37 (s, 12H).
  • 9
  • [ 62224-25-3 ]
  • [ 935685-88-4 ]
  • [ 1232069-34-9 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In 1,2-dimethoxyethane at 50℃; Inert atmosphere; 10 3-{3-(3-Chloro-4-fluorophenyl)-5-[(4-oxoimidazolidin-1-yl)carbonyl]thiophen-2-yl}-5-fluorobenzenecarbonitrile Example 10 3-{3-(3-Chloro-4-fluorophenyl)-5-[(4-oxoimidazolidin-1-yl)carbonyl]thiophen-2-yl}-5-fluorobenzenecarbonitrile Under argon, 1.50 g (4.78 mmol) of the compound from Example 8A are provided in 75 ml of 1,2-dimethoxyethane, and 1.30 g (5.26 mmol) of the compound from Example 5A, 4.67 g (14.3 mmol) of cesium carbonate, 159 mg (0.33 mmol) of dicyclohexyl[2',4',6'-tri(propan-2-yl)biphenyl-2-yl]phosphane and 32.0 mg (0.14 mmol) of palladium(II) acetate are added. The mixture is stirred at 50° C. overnight. Water is subsequently added, the mixture is extracted with ethyl acetate and the extract is dried over sodium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient with addition of 0.1% formic acid). 1.05 g of ethyl 4-bromo-5-(3-cyano-5-fluorophenyl)thiophene-2-carboxylate are obtained. LC-MS (Method 1): Rt=2.91 min; MS (ESIpos): m/z=354 [M+H]+.
  • 10
  • [ 935685-88-4 ]
  • [ 1232068-69-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / palladium diacetate; XPhos / 1,2-dimethoxyethane / 50 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere 3: water; lithium hydroxide / tetrahydrofuran / 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 20 °C
  • 11
  • [ 935685-88-4 ]
  • [ 1232069-37-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / palladium diacetate; XPhos / 1,2-dimethoxyethane / 50 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere
  • 12
  • [ 935685-88-4 ]
  • [ 1256373-91-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / palladium diacetate; XPhos / 1,2-dimethoxyethane / 50 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 80 °C / Inert atmosphere 3: water; lithium hydroxide / tetrahydrofuran / 20 °C
  • 13
  • [ 935685-88-4 ]
  • [ 1231208-88-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate; XPhos / palladium diacetate / 1,2-dimethoxyethane / 48 h / 50 °C / Inert atmosphere 2: water; lithium hydroxide / tetrahydrofuran / 20 °C 3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 20 °C
  • 14
  • [ 935685-88-4 ]
  • [ 1231209-20-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; XPhos / palladium diacetate / 1,2-dimethoxyethane / 48 h / 50 °C / Inert atmosphere 2: water; lithium hydroxide / tetrahydrofuran / 20 °C
  • 15
  • [ 935685-88-4 ]
  • [ 1231208-93-7 ]
  • [ 1231209-02-1 ]
YieldReaction ConditionsOperation in experiment
8% With caesium carbonate; XPhos In 1,2-dimethoxyethane at 50℃; for 48h; Inert atmosphere; 15A ethyl 5-(3-chloro-4-fluorophenyl)-4-(3-cyano-5-fluorophenyl)furan-2-carboxylate Under argon, 400 mg (1.15 mmol) of the compound from Example 6A and 313 mg (1.27 mmol) of the compound from Example 4A are provided in 11 ml of 1,2-dimethoxyethane, and 1.12 g (3.45 mmol) of cesium carbonate, 38.4 mg (0.08 mmol) of dicyclohexyl[2',4',6'-tri(propan-2-yl)biphenyl-2-yl]phosphane and 7.8 mg (0.04 mmol) of palladium(II) acetate are added. The mixture is stirred at 50° C. for two days. The mixture is concentrated and the residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 34.0 mg (8% of theory) of the title compound are obtained.1H-NMR (400 MHz, DMSO-d6): δ=7.90 (ddd, 1H), 7.83 (t, 1H), 7.76 (s, 1H), 7.74-7.68 (m, 2H), 7.53 (t, 1H), 7.47 (ddd, 1H), 4.35 (q, 2H), 1.32 (t, 3H).LC-MS (Method 1): Rt=3.04 min; MS (ESIpos): m/z=388 [M+H]+.
  • 16
  • [ 935685-88-4 ]
  • (3-cyano-5-fluorophenyl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With sodium periodate; ammonium acetate In water; acetone at 20℃; 22A Example 22A
(3-Cyano-5-fluorophenyl)boronic acid Example 22A (3-Cyano-5-fluorophenyl)boronic acid 1.00 g (4.05 mmol) of the compound from Example 21A is provided in 40 ml of acetone, 2.60 g (12.1 mmol) of sodium periodate, 0.70 g (9.11 mmol) of ammonium acetate and 40 ml of water are added and the mixture is stirred at room temperature overnight. The mixture is subsequently concentrated, a 2N aqueous sodium hydroxide solution is added to the residue and the precipitate that remains is filtered off with suction. Using a concentrated aqueous hydrogen chloride solution, the solution is adjusted to pH 3 and cooled to 0° C. The precipitate formed is collected by suction filtration, washed with water and dried under high vacuum. 384 mg (58% of theory) of the title compound are obtained. 1H-NMR (400 MHz, DMSO-d6): δ=8.57 (s, 2H), 7.98 (s, 1H), 7.88 (ddd, 1H), 7.84 (dd, 1H). LC-MS (Method 7): Rt=1.07 min; MS (ESIneg): m/z=164 [M-H]-.
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  • [ 935685-88-4 ]
  • [ 1266520-50-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium periodate; ammonium acetate / water; acetone / 20 °C 2: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 1 h / 20 °C / Reflux
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