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[ CAS No. 1150114-77-4 ]

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Chemical Structure| 1150114-77-4
Chemical Structure| 1150114-77-4
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Product Details of [ 1150114-77-4 ]

CAS No. :1150114-77-4 MDL No. :MFCD07644472
Formula : C7H5BFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :164.93 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1150114-77-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1150114-77-4 ]

  • Downstream synthetic route of [ 1150114-77-4 ]

[ 1150114-77-4 ] Synthesis Path-Downstream   1~16

  • 1
  • 5-Chloroisoxazole-3-carboxylic Acid Ethyl Ester [ No CAS ]
  • [ 1150114-77-4 ]
  • [ 1415836-73-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,4-dioxane at 140℃; for 0.583333h; Inert atmosphere; Microwave irradiation; 39 5-(4-Cvano-2-fluor -phenyl)-isoxazole-3-carboxylic acid ethyl esterA mixture of 5-chloro-isoxazole-3-carboxylic acid ethyl ester (600 mg), 4-cyano-2- fluorophenylboronic acid (665 mg), and aqueous Na2CO3 solution (2 M; 4.41 mL) in 1 ,4-dioxane (15 mL) is purged with argon for 15 min prior to the addition of Pd(PPh3) (276 mg). The reaction mixture is heated under an argon atmosphere to 140°C for 20 min in a microwave oven. The solvent is evaporated in vacuo and the residue is mixed with water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 80:20→50:50). LC (method 19): tR = 1 .50 min; Mass spectrum (ESI+): m/z = 261 [M+H]+.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 140℃; for 0.583333h; Inert atmosphere; Microwave irradiation; 39 Intermediate 39 5-(4-Cyano-2-fluoro-phenyl)-isoxazole-3-carboxylic acid ethyl ester 5-(4-Cyano-2-fluoro-phenyl)-isoxazole-3-carboxylic acid ethyl ester A mixture of 5-chloro-isoxazole-3-carboxylic acid ethyl ester (600 mg), 4-cyano-2-fluorophenylboronic acid (665 mg), and aqueous Na2CO3 solution (2 M; 4.41 mL) in 1,4-dioxane (15 mL) is purged with argon for 15 min prior to the addition of Pd(PPh3)4 (276 mg). The reaction mixture is heated under an argon atmosphere to 140° C. for 20 min in a microwave oven. The solvent is evaporated in vacuo and the residue is mixed with water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 80:20→50:50). LC (method 19): tR=1.50 min; Mass spectrum (ESI+): m/z=261 [M+H]+.
Stage #1: 5-Chloroisoxazole-3-carboxylic Acid Ethyl Ester; (4-cyano-2-fluorophenyl)boronic acid With sodium carbonate In 1,4-dioxane; water for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) at 140℃; for 0.333333h; Inert atmosphere; Microwave irradiation; 5-(4-Cyano-2-fluoro-phenyl)-isoxazole-3-carboxylic acid ethyl ester 5-(4-Cyano-2-fluoro-phenyl)-isoxazole-3-carboxylic acid ethyl ester A mixture of 5-chloro-isoxazole-3-carboxylic acid ethyl ester (600 mg), 4-cyano-2-fluorophenylboronic acid (665 mg), and aqueous Na2CO3 solution (2 M; 4.41 mL) in 1,4-dioxane (15 mL) is purged with argon for 15 min prior to the addition of Pd(PPh3)4 (276 mg). The reaction mixture is heated under an argon atmosphere to 140° C. for 20 min in a microwave oven. The solvent is evaporated in vacuo and the residue is mixed with water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate 80:20→50:50). LC (method 3): tR=1.50 min; Mass spectrum (ESI+): m/z=261 [M+H]+.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 140℃; for 0.583333h; Inert atmosphere; Microwave irradiation;

  • 2
  • [ 5419-55-6 ]
  • [ 887266-99-1 ]
  • [ 1068-55-9 ]
  • [ 1150114-77-4 ]
YieldReaction ConditionsOperation in experiment
55% With hydrogenchloride; In tetrahydrofuran; diethyl ether; water; ethyl acetate; Step 1: (4-Cyano-2-fluorophenyl)boronic acid 24.3 ml (48.6 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were added dropwise to a solution of 10.0 g (40.5 mmol) of <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> in a mixture of 120 ml of anhydrous THF and 120 ml of anhydrous diethyl ether at -78 C. When the addition had ended, the mixture was stirred further at -78 C. for another 75 min. 15 ml (64.8 mmol) of triisopropyl borate were then added dropwise. The mixture was then stirred at -78 C. for a further 15 min, before the cold bath was removed and the reaction mixture was allowed to warm to RT. After 3 h at RT, 80 ml of 2 M hydrochloric acid were added and the mixture was stirred intensively at RT for 20 min. Thereafter, it was diluted with approx. 400 ml of water. The phases were separated and the aqueous phase was extracted three times with approx. 150 ml of ethyl acetate each time. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the mixture was filtered and the filtrated was concentrated to dryness on a rotary evaporator. 3.68 g (55% of th.) of the title compound were obtained, this being employed for subsequent reactions without further purification. LC/MS (method F, ESIneg): Rt=0.53 min, m/z=164 [M-H]-.
  • 3
  • [ 1150114-77-4 ]
  • [ 24265-23-4 ]
  • [ 1227159-91-2 ]
YieldReaction ConditionsOperation in experiment
43% With potassium phosphate; palladium diacetate; XPhos; In tetrahydrofuran; dichloromethane; Step 3: 4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorobenzonitrile A mixture of 300 mg (1.84 mmol) of the compound from Example 112A/step 2, 334 mg (2.02 mmol) of the compound from Example 112A/step 1, 8 mg (0.037 mmol) of palladium(II) acetate, 1.17 g (5.52 mmol) of potassium phosphate and 44 mg (0.092 mmol) of 2-dicyclohexylphosphine-2',2',6'-triisopropylbiphenyl (XPhos) in 4 ml of anhydrous THF was degassed, and stirred at 80 C. under argon in a microwave oven (CEM Discover, initial irradiation power 250 W) for 1 h. After cooling to RT, all the volatile constituents were removed on a rotary evaporator. The product was isolated from the residue by means of MPLC (approx. 50 g of silica gel, mobile phase: cyclohexane/methylene chloride 100:0,?5:50?5:95). 160 mg (43% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 7.42 (d, 1H), 7.37 (d, 1H), 7.36 (d, 1H), 6.18 (m, 1H), 4.33 (m, 2H), 3.92 (t, 2H), 2.52-2.48 (m, 2H). GC/MS (method L, ESIpos): Rt=5.79 min, m/z=203 [M]+.
  • 4
  • [ 1150114-77-4 ]
  • [ 24265-23-4 ]
  • [ 1227159-92-3 ]
  • 5
  • [ 1150114-77-4 ]
  • [ 1382136-80-2 ]
  • [ 1451163-56-6 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 160℃; for 0.75h; Microwave irradiation; Inert atmosphere; 3 4-[5-Chloro-2-(4-cvano-2-fluoro-phenyl)-pyridin-4-ylethvnyl1-piperidine-1 -carboxylic acid tert-butyl ester A flask charged with a stir bar, 4-(2,5-dichloro-pyridin-4-ylethynyl)-piperidine-1 - carboxylic acid tert-butyl ester (0.30 g), 4-cyano-2-fluoro-phenylboronic acid (0.20 g), 2 M aqueous Na2CO3 solution (1 ml_), and 1 ,4-dioxane (3 ml_) is sparged with Ar for 10 min. Tetrakis(triphenylphosphine)palladium(0) (40 mg) is added and the resulting mixture is stirred in a microwave over at 160 °C for 45 min. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate.The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 85:15) to give the title compound. LC (method 3): tR = 1 .70 min; Mass spectrum (EST): m/z = 440/442 (CI) [M+H]+.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 60℃; for 0.75h; Inert atmosphere; Microwave irradiation; intermediate 3 4-[5-Chloro-2-(4-cyano-2-fluoro-phenyl)-pyridin-4-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester 4-[5-Chloro-2-(4-cyano-2-fluoro-phenyl)-pyridin-4-ylethynyl]-piperidine-1-carboxylic acid tert-butyl ester A flask charged with a stir bar, 4-(2,5-dichloro-pyridin-4-ylethynyl)-piperidine-1-carboxylic acid tert-butyl ester (0.30 g), 4-cyano-2-fluoro-phenylboronic acid (0.20 g), 2 M aqueous Na2CO3 solution (1 mL), and 1,4-dioxane (3 mL) is sparged with Ar for 10 min. Tetrakis(triphenylphosphine)palladium(0) (40 mg) is added and the resulting mixture is stirred in a microwave over at 160° C. for 45 min. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 85:15) to give the title compound. LC (method 3): tR=1.70 min; Mass spectrum (ESI+): m/z=440/442 (Cl) [M+H]+.
  • 6
  • [ 1150114-77-4 ]
  • [ 1449475-32-4 ]
  • tert-butyl ((1R,2R)-1-(5-(4-cyano-2-fluorophenyl)-1H-benzo[d]imidazol-2-yl)-2-methoxypropyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate In tetrahydrofuran; water at 60℃; for 18h; Inert atmosphere; tert-Butyl ((1R,2R)-1-(5-(4-cyano-2-fluorophenyl)-1H-benzo[d]imidazol-2-yl)-2-methoxypropyl)carbamate. To tert-butyl ((1R,2R)-1-(5-bromo-1H-benzo[d]imidazol-2-yl)-2-methoxypropyl)carbamate (120 mg, 0.312 mmol) in THF/water (5 mL/1 mL) was added 2-fluoro-4-cyanophenylboronic acid (77 mg, 0.531 mmol) and sodium carbonate (83mg, 0.780 mmol) and the mixture degassed with nitrogen for 10 minutes. Dichloro [1,1' bis(di-tert-butylphosphino)]ferrocene palladium (II) (6 mg, 0.00937 mmol) was added and the reaction heated to 60C for 18 hours. The reaction was cooled and filtered through celite. The filtrate was diluted with water and extracted with EtOAc (3 x 20 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography to provide 96 mg (68%) of the desired product. 1H NMR (400 MHz, CD3OD) δ 7.70-7.78 (m, 2H), 7.61-7.70 (m, 3H), 7.46 (d, J=8.40 Hz, 1H), 4.95 (s, 1H), 3.84-3.97 (m, 1H), 3.27 (s, 3H), 1.47 (br. s., 9H), 1.21 (d, J=6.25 Hz, 3H). MS m/z 425.14 [M+H]+
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium carbonate In tetrahydrofuran; water at 60℃; for 18h; Inert atmosphere; 90 Example 90 Example 90 4-{2-[(1 R,2R)-1 -Amino- -methoxypropyl1-1 H-benzimidazol-5-yl)-3-fluorobenzonitrile To te/t-butyl [(1 R,2R)-1 -(5-bromo-1 H-benzimidazol-2-yl)-2-methoxypropyl]carbamate (Preparation 22, 120 mg, 0.312 mmol) in THF/water (5 mL/1 ml_) was added 2- fluoro-4-cyanophenylboronic acid (77 mg, 0.531 mmol) and sodium carbonate (83 mg, 0.780 mmol) and the mixture degassed with nitrogen for 10 minutes. Dichloro [1 ,1 ' bis(di-terf-butylphosphino)]ferrocene palladium (II) (6 mg, 0.00937 mmol) was added and the reaction heated to 60°C for 18 hours. The reaction was cooled and filtered through celite. The filtrate was diluted with water and extracted with EtOAc (3 x 20 ml_). The organic layers were combined, dried over Na2SO and concentrated in vacuo. The residue was purified using silica gel column chromatography and dissolved in a mixture of TFA and DCM (1 mL/5 ml_). The reaction was stirred at room temperature for 3 hours before concentrating in vacuo. The residue was purified by filtering through Amberlist-21 followed by reverse phase column chromatography eluting with 0-40% acetonitrile in 0.1 % formic acid in water to afford the title compound as the formate salt (32 mg, 30%). 1H NMR (400MHz, MeOD): δ ppm 1 .18 (s, 3H), 3.43 (s, 3H), 3.87 (br s, 1 H), 4.32 (br s, 1 H), 7.52 (d, 1 H), 7.65-7.80 (m, 4H), 7.87 (br s, 1 H). LCMS (4.5 minute run) Rt = 1 .79 minutes MS m/z 325 [M+H]+
  • 7
  • [ 1150114-77-4 ]
  • [ 1464153-45-4 ]
  • [ 1464150-70-6 ]
YieldReaction ConditionsOperation in experiment
9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 140℃; for 0.25h; Inert atmosphere; Microwave irradiation; 35 Example 35: 3 -fluoro-4-(6-(4-(4-methylpiperazine- 1 -carbon yl)phenyl)imidazof 1 ,2-fl~]pyrazin- -yl)benzonitrile To a solution of (4-(3-iodoimidazo[l,2-a]pyrazin-6-yl)phenyl)(4-methylpiperazin-l- yl)methanone (200 mg, 0.45 mmol) in a mixture of toluene (4 mL) and ethanol (2 ml) under inert atmosphere, was added K2C03 (124 mg, 0.89 mmol), 4-cyano-2-fluorophenylboronic acid (88 mg, 0.54 mmol) and Pd(PPh3)4 (52 mg, 0.045 mmol). The resulting mixture was heated in a microwave reactor at 140 °C for 15 min, and then was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent CH2Cl2/MeOH 95:5 to 90: 10) to afford 3-fluoro-4-(6-(4-(4-methylpiperazine- 1 - carbonyl)phenyl)imidazo[l,2-fl]pyrazin-3-yl)benzonitrile (18.1 mg, 9%, AUC HPLC 96%) as a yellow solid. FontWeight="Bold" FontSize="10" H NMR (400 MHz, CD3OD) δ 9.21 (s, 1H), 8.74 (d, J= 1.5 Hz, 1H), 8.12 (d, J= 8.2 Hz, 2H), 8.10 (s, 1H), 8.00-7.96 (m, 1H), 7.89-7.87 (m, 1H), 7.82 (d, J= 8.0 Hz, 1H), 7.54 (d, J= 8.2 Hz, 2H), 3.81 (bs, 2H), 3.53 (bs, 2H), 2.55-2.52 (m, 4H), 2.36 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 171.97, 160.63, 143.81, 142.39, 140.94, 139.19, 138.00, 136.99, 133.17, 130.43, 128.75, 127.91, 122.44, 122.00, 121.61, 118.25, 116.42, 115.57, 55.98, 55.58, 46.01; MS (ESI) m/z 441 [C25H21FN60 + H]+.
9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 140℃; for 0.25h; Inert atmosphere; Microwave irradiation; 35 Example 35 To a solution of (4-(3-iodoimidazo[1,2-a]pyrazin-6-yl)phenyl)(4-methylpiperazin-1-yl)methanone (200 mg, 0.45 mmol) in a mixture of toluene (4 mL) and ethanol (2 ml) under inert atmosphere, was added K2CO3 (124 mg, 0.89 mmol), 4-cyano-2-fluorophenylboronic acid (88 mg, 0.54 mmol) and Pd(PPh3)4 (52 mg, 0.045 mmol). The resulting mixture was heated in a microwave reactor at 140° C. for 15 min, and then was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent CH2Cl2/MeOH 95:5 to 90:10) to afford 3-fluoro-4-(6-(4-(4-methylpiperazine-1-carbonyl)phenyl)imidazo[1,2-c]pyrazin-3-yl)benzonitrile (18.1 mg, 9%, AUC HPLC 96%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 9.21 (s, 1H), 8.74 (d, J=1.5 Hz, 1H), 8.12 (d, J=8.2 Hz, 2H), 8.10 (s, 1H), 8.00-7.96 (m, 1H), 7.89-7.87 (m, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.54 (d, J=8.2 Hz, 2H), 3.81 (bs, 2H), 3.53 (bs, 2H), 2.55-2.52 (m, 4H), 2.36 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 171.97, 160.63, 143.81, 142.39, 140.94, 139.19, 138.00, 136.99, 133.17, 130.43, 128.75, 127.91, 122.44, 122.00, 121.61, 118.25, 116.42, 115.57, 55.98, 55.58, 46.01; MS (ESI) m/z 441 [C25H21FN6O+H]+.
  • 8
  • [ 1150114-77-4 ]
  • [ 460081-18-9 ]
  • [ 1557037-79-2 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 150℃;Inert atmosphere; Microwave irradiation; 2-(4-Cyano-2-fluoro-phenyl)-oxazole-4-carboxylic acid ethyl ester A mixture of <strong>[460081-18-9]2-chloro-oxazole-4-carboxylic acid ethyl ester</strong> (250 mg), 4-cyano-2-fluorophenylboronic acid (277 mg), tetrakis-(triphenylphosphine)-palladium (115 mg), and aqueous Na2CO3 solution (2 M; 1.84 mL) in 1,4-dioxane (10 mL) is heated to 150 C. under an argon atmosphere in a microwave oven. The reaction mixture is concentrated in vacuo. The residue is stirred in methanol for two days, filtered off and dried to give the title product. LC (method 8): tR=1.41 min; Mass spectrum (ESI+): m/z=261 [M+H]+.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 150℃;Inert atmosphere; Microwave irradiation; Intermediate 272-(4-Cyano-2-fluoro-henyl)-oxazole-4-carboxylic acid ethyl ester: A mixture of <strong>[460081-18-9]2-chloro-oxazole-4-carboxylic acid ethyl ester</strong> (250 mg), 4-cyano-2- fluorophenylboronic acid (277 mg), tetrakis-(triphenylphosphine)-palladium (115 mg), and aqueous Na2003 solution (2 M; 1 .84 mL) in 1 ,4-dioxane (10 mL) is heated to150C under an argon atmosphere in a microwave oven. The reaction mixture is concentrated in vacuo. The residue is stirred in methanol for two days, filtered off and dried to give the title product. LC (method 8): tR = 1 .41 mm; Mass spectrum (ESI):mlz = 261 [M+H]
  • 9
  • [ 1150114-77-4 ]
  • (2R)-4-(6-bromo-1-oxoisoquinolin2(1H)-yl)-2-methyl-2-(methylsulfonyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide [ No CAS ]
  • (2R)-4-(6-(4-cyano-2-fluorophenyl)-1-oxoisoquinolin-2(1H)-yl)-2-methyl-2-(methylsulfonyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate at 110℃; for 0.5h; Microwave irradiation; 59.A` PdCI2(dppf) (29.2 mg, 0.04 mmol), (2R)-4-(6-bromo-1 -oxoisoquinolin-2(1 H)-yl)-2-methyl- 2-(methylsulfonyl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide (Intermediate 10) (200 mg, 0.399 mmol) and (4-cyano-2-fluorophenyl)boronic acid (86 mg, 0.519 mmol) and heated in a microwave to 1 10 °C for 30 min. The organic phase was diluted with DCM (20 ml_) and extracted with DCM (10ml x 3) and the combined organic layers were washed with water (20 ml_), brine (30 ml_), dried over sodium sulphate and concentrated. The residue was purified by silica gel chromatography (EtOAc/DCM: 10-100%) to give (2R)-4- (6-(4-cyano-2-fluorophenyl)-1 -oxoisoquinolin-2(1 H)-yl)-2-methyl-2-(methylsulfonyl)-N- ((tetrahydro-2H-pyran-2-yl)oxy)butanamide (159 mg, 0.294 mmol, 74 % yield) as colorless oil. LCMS: [M+Na] 564.3.
  • 10
  • [ 1150114-77-4 ]
  • 6-bromo-4-iodoisoquinoline [ No CAS ]
  • C16H8BrFN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere; Synthesis of compound 8-b Under N2 atmosphere, compound 4-c (330mg, 1mmol), 2-fluoro-4-cyanophenylboronic acid (165mg, 1mmol)and sodium carbonate (212mg, 0.2mmol) were suspended in a mixed solution of dioxane (4mL) and water (1mL), [1,1’-bis(diphenylphosphine)ferrocene]palladium dichloride (56mg, 0.1mmol) was added. The mixture was stirred at 80 °Cfor 3hrs, cooled to room temperature, filtered through celite, the filtrate cake was washed with EA (20mL). The filtratewas in turn washed with water (10mL33) and saturated brine (lOmL), dried over anhydrous magnesium sulfate, filtered,concentrated under reduced pressure. The residue was purified by silica column chromatography (PE:EA = 3:1) to givecompound 8-b (63mg, yield 19%). LC-MS (ESI): m/z = 387 [M+H]+.
  • 11
  • [ 175278-30-5 ]
  • [ 1150114-77-4 ]
  • 4'-bromo-2'-ethyl-2-fluoro-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]
  • 12
  • [ 160599-70-2 ]
  • [ 1150114-77-4 ]
  • C12H5BrClFN2 [ No CAS ]
  • 13
  • [ 7238-61-1 ]
  • [ 1150114-77-4 ]
  • 3-fluoro-4-(4-methylthiazol-2-yl)benzonitrile [ No CAS ]
  • 14
  • [ 5419-55-6 ]
  • [ 887266-99-1 ]
  • [ 1150114-77-4 ]
  • 15
  • [ 1150114-77-4 ]
  • C16H8ClN3 [ No CAS ]
  • C23H11FN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; 4.4-1 4-1) Preparation of compound 4-1 2-chlorodibenzo[b,e]pyrimido[4,5,6-gh]pyrrolysine 20g (72 mmol), 4-cyano-2-fluorophenylboronic acid 13.1g (79.2 mmol) , Pd(PPh3)44.2 g (3.6 mmol), potassium carbonate 20 g (144 mmmol) were suspended in 360 ml of toluene, 70 ml of ethyl alcohol, and 70 ml of distilled water, followed by reflux agitation for 12 hours.After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and purified by a silica gel column to obtain compound 4-1, 19.6 g (yield: 75%).
  • 16
  • [ 842145-02-2 ]
  • [ 1150114-77-4 ]
  • ethyl 6-(4-cyano-2-fluorophenyl)-4-(isopropylamino)-5-nitronicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; toluene at 80℃; 1 Intermediate IB: Ethyl 6-(4-cyano-2-fluorophenyl)-4-(isopropylamino)-5-nitronicotinate A mixture of ethyl 6-chloro-4-(isopropylamino)-5-nitronicotinate (67 mg, 0.23 mmol), (4-cyano-2-fluorophenyl)boronic acid (42.2 mg, 0.26 mmol), sodium carbonate (49.4 mg, 0.47 mmol), and bis(triphenylphosphine)palladium(II) dichloride (16.4 mg, 0.023 mmol) in EtOH (1.5 mL) and toluene (2 mL) was degassed with nitrogen and stirred at 80 °C overnight. The reaction mixture was concentrated, diluted with EtOAc, washed with water, and the organic layer was dried (MgSOr), and concentrated. The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford ethyl 6-(4-cyano-2-fluorophenyl)-4-(isopropylamino)- 5-nitronicotinate (50.7 mg, 59% yield) as a yellowish brown solid. NMR (400 MHz, CHLOROFORM-d) d 9.03-8.95 (m, 2H), 7.57-7.43 (m, 3H), 4.43 (q, J=1.1 Hz, 2H), 3.54 (dt, =8.8, 6.3 Hz, 1H), 1.47-1.41 (m, 3H), 1.28-1.22 (m, 6H). LCMS m/z 373.1 (M+l).
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[ 957121-05-0 ]

(3-Cyano-2-fluorophenyl)boronic acid

Similarity: 0.89

Organoboron

Chemical Structure| N/A

[ N/A ]

4-cyano-2,6-difluorophenylboronicacid

Similarity: 0.98

Chemical Structure| 2199440-52-1

[ 2199440-52-1 ]

4-Cyano-2,6-difluorophenylboronic acid

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Chemical Structure| 2199440-52-1

[ 2199440-52-1 ]

4-Cyano-2,6-difluorophenylboronic acid

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Chemical Structure| 468718-30-1

[ 468718-30-1 ]

5-Cyano-2-fluorobenzeneboronic acid

Similarity: 0.95

Chemical Structure| 468718-30-1

[ 468718-30-1 ]

5-Cyano-2-fluorobenzeneboronic acid

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Aryls

Chemical Structure| 468718-30-1

[ 468718-30-1 ]

5-Cyano-2-fluorobenzeneboronic acid

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Chemical Structure| 656235-44-8

[ 656235-44-8 ]

(2-Cyano-6-fluorophenyl)boronic acid

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Chemical Structure| 170981-26-7

[ 170981-26-7 ]

(2-Fluoro-4-methylphenyl)boronic acid

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Chemical Structure| 957121-05-0

[ 957121-05-0 ]

(3-Cyano-2-fluorophenyl)boronic acid

Similarity: 0.89

Organoboron

Chemical Structure| N/A

[ N/A ]

4-cyano-2,6-difluorophenylboronicacid

Similarity: 0.98

Chemical Structure| 2199440-52-1

[ 2199440-52-1 ]

4-Cyano-2,6-difluorophenylboronic acid

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Chemical Structure| 2199440-52-1

[ 2199440-52-1 ]

4-Cyano-2,6-difluorophenylboronic acid

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Chemical Structure| 468718-30-1

[ 468718-30-1 ]

5-Cyano-2-fluorobenzeneboronic acid

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Chemical Structure| 468718-30-1

[ 468718-30-1 ]

5-Cyano-2-fluorobenzeneboronic acid

Similarity: 0.95