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[ CAS No. 548797-51-9 ]

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Chemical Structure| 548797-51-9
Chemical Structure| 548797-51-9
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CAS No. :548797-51-9 MDL No. :MFCD16996249
Formula : C13H15BClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :263.53 g/mol Pubchem ID :-
Synonyms :

Safety of [ 548797-51-9 ]

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

Application In Synthesis of [ 548797-51-9 ]

  • Downstream synthetic route of [ 548797-51-9 ]

[ 548797-51-9 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 154607-01-9 ]
  • [ 73183-34-3 ]
  • [ 548797-51-9 ]
YieldReaction ConditionsOperation in experiment
100% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 115℃; for 12h; Under N2 atmosphere, bis(pinacolato)diboron (391mg, 1.54mmol), potassium acetate (412mg, 4.2mmol) and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (102mg, 0.14mmol) were respectively added to a solution of 2-chloro-4-bromobenzonitrile (300mg, 1.4mmol) in dioxane (15mL). The mixture was stirred at 115C for 12hrs, cooled to room temperature, filtered through celite, washed with EA (50mL). The filtrate was evaporated under reduced pressure to give compound 22-c (620mg, yield 100%). The product was directly used for the next step without further purification. LC-MS (ESI): m/z = 182 [M+H]+.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 14h; Reference Example 25; 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 4-Bromo-2-chlorobenzonitrile (19.43 g), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolan (25.08 g), potassium acetate (26.5 g), and 1,1'-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex (1:1) (2.20 g) were dissolved in DMSO (300 mL), and the mixture was stirred at 80 C. for 14 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was suspended in diisopropyl ether-hexane and filtrated to give the title compound (17.74 g) as a brown powder.1H-NMR (CDCl3) δ: 1.35 (12H, s), 7.63-7.68 (1H, m), 7.72-7.80 (1H, m), 7.91 (1H, s).
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 4.5h; Example 15: Synthesis of 2-Chloro-4-(5-fluoro-4-hydroxymethyl-pyridin-3-yl)- benzonitrileStep 1: 2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzonitrile (15a)A mixture of 4-bromo-2-chlorobenzonitrile (15 g, 69.3 mmol), 4,4,4' ,4', 5,5,5', 5'-octamethyl- 2,2'-bi(1 ,3,2-dioxaborolane) (17.60 g, 69.3 mmol), potassium acetate (13.60 g, 139 mmol) and PdCI2(dppf).CH2CI2 adduct (2.83 g, 3.46 mmol) in 1 ,4-dioxane (100 mL) was heated to 80 C for 4.5 hr. After filtration and concentration, the residue was dissolved into CH2CI2 and mixed with celite. After concentration, the residue was loaded to column (120g ISCO) and flushed with ethyl acetate / heptane (v/v, 0%-5%) and resulted colorless solid 16.4 g. 1H NMR (400.3 MHz, CDCI3): 6 1.35 (s, 12H), 7.61 (d, J = 7.6 Hz, 1H), 7.70 (d, J =7.6 Hz, 1 H), 7.87 (s, 1 H).
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 4.5h; A mixture of 4-bromo-2-chlorobenzonitrile (15 g, 69.3 mmol), 4,4,44',5,5,5',5'- octamethyl-2.2'-bi(1,3,2-dioxaborolane) (17.6O g, 69.3 mmol). potassium acetate (13.60 g, 139 mmof) and PdCI2(dppf).CH2CI2 addυct (2.83 g, 3.46 mmol) in 1,4-dioxane (100 mL) was heated to 800C for 4.5 h. After filtration and concentration, the residue was dissolved into CH2Ci2 and mixed with celite. After concentration, the residue was loaded to column (12Og isco) and flushed with ethyl acetate / heptane (v/v, 0%-5%) and resulted in a colorless solid 16.4 g. 1H NMR (400 MHz1 CDCI3)'. δ 1.35 (s. 12H), 7.61 (d, J = 7.6 Hz. 1H), 7.70 (d, J «7.6 Hz. 1H), 7.87 (s. 1H).
0.850 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 4h; The title compound was prepared following the procedure described in step-3 of Intermediate- 33 by using 4-bromo-2-chlorobenzonitrile (1.0 g, 4.61 mmo), 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (1.29 g, 4.33 mmol), potassium acetate (0.9063 g, 9.23 mmol),Pd(dppf)C12 (0.190 g, 0.23 mmol) in 1,4-dioxane to afford 0.850 g of title compound. ‘HNMR (300 MHz, DMSO-d6): 7.99-7.91 (d, J = 7.8Hz, 1H), 7.82 (s, 1H), 7.75-7.73 (d, J =7.2 Hz, 1H), 1.31 (s, 12H):_To a solution of ethyl 4-amino-3-bromobenzoate (5.0 g, 20.66 mmol), (4- cyanophenyl)boronic acid (3.33 g, 22.72 mmol) and Pd(dppf)C12 (0.843 g, 1.03 mmoi) indiglyme (10 mL) was added K2C03 (4.27 g, 30.99 mmol). The reaction mixture was heated at80C for 4 h. The reaction mass was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine. The organic layer was separated, dried, filtered and concentrated to afford 2.7 g of title product. ‘H NMR (300 MHz, DMSO-d6): 7.92-7.89 (d, J = 7.8 Hz, 2H), 7.69-7.67 (d, J = 8.7 Hz, 1H), 7.63-7.60 (d, J = 7.8 Hz, 2H),7.56 (s, 1H), 6.8 1-6.78 (d, J = 8.4Hz, 1H), 5.83 (br s, 2H), 4.22-4.20 (q, J = 6.9 Hz, 2H),1.28-1.23 (t, J= 7.5 Hz, 3H).

  • 2
  • [ 548797-51-9 ]
  • [ 1126779-45-0 ]
  • [ 1126777-63-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In tetrahydrofuran; water; for 8h;Reflux; Inert atmosphere; Example 289; Ethyl 1-[4-(tert-butoxycarbonyl)benzyl]-4-(3-chloro-4-cyanophenyl)-5-methyl-1H-pyrazole-3-carboxylate Ethyl 4-bromo-1-[4-(tert-butoxycarbonyl)benzyl]-5-methyl-1H-pyrazole-3-carboxylate (1.78 g) synthesized in Reference Example 24, <strong>[548797-51-9]2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile</strong> (2.21 g) synthesized in Reference Example 25 and triethylamine (1.17 mL) were dissolved in THF-water (6:1) (9.8 mL), and 1,1'-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex (1:1) (343.0 mg) was added under a nitrogen atmosphere. The reaction mixture was stirred with heating under reflux for 8 hr, poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (hexane-ethyl acetate) to give the title compound (1.10 g) as colorless crystals.1H-NMR (CDCl3) δ: 1.29 (3H, t), 1.57 (9H, s), 2.09 (3H, s), 4.33 (2H, q), 5.49 (2H, s), 7.20 (2H, d), 7.29 (1H, dd), 7.45 (1H, d), 7.68 (1H, d), 7.98 (2H, d).
  • 3
  • [ 13535-01-8 ]
  • [ 548797-51-9 ]
  • [ 1255870-55-3 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 95℃; for 18h; (General Suzuki reaction procedure 1) A mixture of 2-chloro-4-(4,4.5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)benzonitrile (1.32 g, 5 mmol), 5-Bromo-pyridin«3-ylamine (865 mg, 5 mmol), s-PHOS (103 mg, 0.25 mmoi), potassium phosphate (2.12 g, 10 mmol) and Pd2(dba)3 (41.2 mg, 0.1 mmol) in toluene (20 mL) was heated to 95 0C overnight (18 h). After filtration and concentration, the residue was dissolved into CH2CI2 and mixed with celite. After concentration, the residue was loaded to column (MeOH-CH2CI2, v/v, 1% - 3.5%) and resulted in a tight brown solid (500 mg). 1HNMR (400 MHz, CDCI3): δ 4.82 (brs, 2H), 7.11 (t, J « 2 Hz, 1H), 7.55 (dd, J = 2 Hz, 8 Hz1 1H), 7.69 (d, J = 2 Hz, 1H)1 7.75 (d, J * 8 Hz, 1H), 8.16 (d, J * 2 Hz. 1H), 8.22 <;d, J = 2 Hz1 1H).
  • 4
  • [ 548797-51-9 ]
  • [ 1255713-75-7 ]
  • [ 1255869-37-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 0.416667h; A mixture of N-({5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide (5 g, 15.66 mmol), 2-chloro-4-(4,4,5,5-tetrarnethyl-1l3,2-dioxaborolan-2-yl)benzonitriie (as prepared in Example 1 step 1; 4.13 g, 15.66 mmol), sodium carbonate (15.66 mL. 31.3 mmol) and PdCI2(dppf) CH2CI2 addυct (0.320 g, 0.392 mmol) in DMF (100 mL) was heated to 100 0C for 25 min. After concentration, the residue was dissolved into CH2Ci2 and filtered through a pad of Na2SO4. The solution was absorbed into celite and concentrated. The residue was purified by flash column (ethyl acetate / heptane, 3G%-50%-80%, v/v) and yielded the title compound as a colorless solid (5.Og). Chiral separation by chiral HPLC (Chiraipak AD-H using Supercritical fluid chromatography. 25% Methanol at 65 grams per minute with supercritical CO2) afforded enantiomer 1 (S)-N-((5-(3-chloro-4- cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide (retention time - 3 min), and enantiomer 2 (R)-N-((5-(3-chloro-4-cyanophenyl)pyridin«3- yl)(cyclopropyl)methyl)ethanesulfonamjde (retention time = 4 min). ESI-MS mlz: 376.2 [M+Hr, 1H NMR (400 MHz, CDCI3): δ 0.37-0.40 (m, 1H), 0.51-0.55 (m, 1H), 0.57-0.68 (m, 1H), 0.70-0.77 (m, 1H), 1.15-1.27 (m, 3H)1 2.70-2.88 (m. 2H), 3.85 (dd, J = 5 Hz, 9 Hz, 1H)1 4.68 (d, J = 5 Hz1 1H), 7.53 (dd, J » 1.5 Hz, 8 Hz, 1H)1 7.67 (d. J * 1.5 Hz. 1H), 7.73 (d, J * 8Hz, 1H), 7.80 (t, J = 2 Hz, 1H), 8.67 (d, J = 2 Hz, 1H), 8.72 (d, J = 2 Hz, 1H).
  • 5
  • [ 548797-51-9 ]
  • [ 1255871-17-0 ]
  • [ 1255869-59-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; A mixture of N-(2«(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamide (30 mg, 0.098 mmol), 2-chloro-4-(4,4,5,5-tetramethyM ,3,2-dioxaborolan~2-yl)benzonitrile (27.0 mg, 0.103 mmol), PdCI2(dppf) CH2CI2 adduct (1.994 mg, 2.441 μmol) and sodium carbonate (98 μl, 0.195 mmol) in DMF (10 mL) was heated to 100 0C overnight. After concentration, the residue was purified by column (MeOH-CH2CI2. v/v, 10-20%) yielded the title compound as oil (1mg). ESI-MS m/z: {M+1)+ 364.0. Retention time * 1.40 min. 1H NMR (400 MHz, CDCI3): δ 1.31 (t, J «7.37 Hz. 3H). 1.76 (s, 6H), 2.86-2.91 (m. 2H), 4.54 (brs, 1H), 7.52 (dd, J »1.7, 8 Hz, 1H), 7.67 (d, J =1.6 Hz. 1H), 7.72 (d. J = 8 Hz, 1H), 7.95 (t, J « 2.2 Hz, 1H). 8.67 (d. J * 2.2 Hz. 1H), 8.76 (d, J «2.2 Hz. 1H).
  • 6
  • [ 548797-51-9 ]
  • [ 173999-31-0 ]
  • [ 1255870-19-9 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 100℃; for 1h;Inert atmosphere; To 2-chloro-4-(4,4.5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (217 mg, 0.824 mmol) in DMF (4 mL) were added 3-bromo-5-(1,1-dioxo-isothiazofidin-2-ylmethyl)- pyridine (200 mg, 0.687 mmol) and 2M aqueous sodium carbonate (0.687 mL, 1.374 mmol). The reaction mixture was flushed and evacuated with N2 thrice followed by the addition of PdCI2(dppf).CH2CI2 adduct (28.0 mg, 0.034 mmol). The reaction mixture was stirred at 1000C for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with water thrice. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The crude was dissolved in OMF (5 mL) and purified using Xbridge C18 eluting with a 10 to 100% ACN-water to afford 2-chloro-4-[5- (1,1-dioxo-isothiazolidin~2-ylmethyl)-pyridin-3-yl]-benzonitrile as a white solid. HRMS: (ESI) m/z 348.0575 [(M+Hγ Calcd for C16H14CIN3O2S 348.0573}. 1H NMR (400 MHz. MeOD) δ ppm 2.33 - 2.47 (m, 2 H), 3.24 - 3.33 (m, 4 H), 4.37 (s, 2 H). 7.87 (dd, J=8.2, 1.6 Hz, 1 H), 7.97 (d. J-BA Hz, 1 H)1 8.06 (d, J=1.5 Hz, 1 H), 8.22 (t, J«2.1 Hz, 1 H), 8.68 (d, >;2.0 Hz, 1 H), 8.87 (d, J-2.Z Hz, 1 H).
  • 7
  • [ 548797-51-9 ]
  • [ 1255871-43-2 ]
  • [ 1255871-45-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 2h; To a suspension of potassium 1-(5-bromopyridin«3-yl)cyclopropanecarboxylate (28 mg, 0.1 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-1>;3,2-dJoxaborolan-2-yl)benzonitrite (26 mg, 0.1 mmol). PdCI2(dppf).CH;.CI2 (4.08 mg, 5.0 μmol) in DMF (1 mL) was added 2M Na2CO3 (0.1 mL, 0.2 mmol). and the mixture was heated to 1000C for 2 h. The mixture was concentrated and purified by silica chromatography eluting with a 0-10% MeOH- DCM gradient to give 1-(5~(3~chloro-4-cyanophenyl)pyridin-3~yl)cyclopropanecarboxylic acid. MS: (ESI) m/z 299.0, 301.0 (M+H)
  • 8
  • [ 548797-51-9 ]
  • [ 1255871-51-2 ]
  • [ 1255871-53-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 85℃; for 7h; To a solution of W-ftS-bromo^-chJoropyridin-S-ylXcyclopropyOmethyO-Λ/- methylmethanesulfonamide (1.03 g, 2.9 mmol) and 2-chloro-4«(4,4.5,5-tetramethyl-1,3,2« dioxaborolan-2-yl)beϖzonitrile (2.29 g, 8.7 mmol) in DMF (20 mL) was added PdCI-(dppf).CH2CI2 (118 mg, 0.145 mmol) and 2M Na?CO3 in water (2.9 mL, 5.8 mmol), and the mixture was heated to 850C for 7 h. The mixture was cooled to room temperature, poured into water (100 mL), extracted with EtOAc (200 ml*3), washed with water (20 mL*3) and dried over Na2SO4. The mixture was purified by silica gei chromatography eluting with a 0-50% EtOAc-heptane gradient to give Λ/-((4-chloro-5-(3- chlorc-4-cyanophenyl)pyridin-3-y.)(cyclopropyl)methyO-W-methylmethanesulfonamide. MS(ESI): m/z ΛWΛ, 412.1 <;M+H)+.
  • 9
  • [ 548797-51-9 ]
  • [ 1255870-99-5 ]
  • [ 1255869-49-8 ]
YieldReaction ConditionsOperation in experiment
33% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere; A mixture of 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-ben2onitϖle (205 mg, 0.77 mmol), N-((5-bromopyridJn-3-yl)(cyclopentyl)methyl)ethane-sulfoϖamJde (270 mg, 0.77 mmol), PdCI2(PPh3);? (45mg, O.Oβmmol) and Na2CO3 (2 M in water, 0.97 mL, 1.94 mmol) in DMF(4 mL) was heated at 10OX for 2h. The solvent was removed in vacuo. The residue was dissolved in DCM and filtered. The DCM layer was concentrated and purified by flash column (EtOAc/Heptane, v/v, 0-50%) to give the title compound (104 mg, 33%); ESI-MS mlr. 404 (M-HJ+; 1HNMR (MeOD, 400 MHz) δ 8.80 (1H, d. J- 2.0Hz). 8.61 (1H, d, J= 2.0Hz), 8.15 (1H, t, J* 2.0Hz). 8.01 (1H, d, J« 1.6Hz), 7.94 (1H, d, J« 8.0Hz), 7.82 (1H1 dd. J- 8.0, 1.6Hz), 4.29 (1H. d, J= 10Hz), 2.92-2.72 (2H1 m), 2.34-2.27 (1H, m), 2.03-1.97 (1H1 m). 1.77-1.53 (6H, m), 1.38-1.28 (1H, m), 1.15 (1H, t, J= 7.2Hz).
  • 10
  • [ 548797-51-9 ]
  • [ 70201-43-3 ]
  • [ 1308669-85-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 120℃; for 3h; Example 20: Synthes -chloro-4-(4-(1-hydroxyethyl)pyridin-3-yl)benzonitrile 20a Step 1: 2-chloro-4-(4-formylpyridin-3-yl)benzonitrile (20a) A mixture of 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (0.264 g, 1 mmol), 3-bromoisonicotinaldehyde (0. 86 g, 1.000 mmol), sodium carbonate (1.000 ml, 2.000 mmoi), bis(triphenylphosphine)palladium(ll) chloride (0.018 g, 0.025 mmol) in DMF (6 mL, dry) was heated to 120 C for 3 hrs. After concentration, the residue was dissolved into CH2CI2-MeOH and mixed with silica gel and concentrated. After flash column (MeOH- CH2CI2, v/v, 0.5% - 1 %) yielded 2-chloro-4-(4-formylpyridin-3-yl)benzonitrile (20a) as colorless solid (170 mg) 1H NMR (400.3 MHz, CDCI3): delta 7.63 (d, J = 8.0 Hz, 1H), 7.79 (s,1H), 7.83 (d, J = 8.0 Hz, 1H), 8.35 (s, 1H), 9.07 (s, 1 H), 9.15 (s, 1H), 10.22 (s, 1 H).
  • 11
  • [ 1064677-18-4 ]
  • [ 548797-51-9 ]
  • [ 1308669-19-3 ]
YieldReaction ConditionsOperation in experiment
52% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere; Step 3: 2-Chloro-4-(5-chloro-4-hydroxymethyl-pyridin-3-yl)-benzonitrile (22)To the solution of 2-Chloro-4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzonitrile (320 mg, 1.21 mmol), (3-Bromo-5-chloro-pyridin-4-yl)-methanol (220 mg, 1.21 mmol) andPdCI2(dppf). CH2CI2 adduct (79 mg, 0.09 mmol) in DMF (4 mL) was added 2M Na2C03 solution (1.82 ml, 3.64 mmol) under Nitrogen atmosphere. The mixture was stirred and heated at 100C for 4hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4CI solution. After extraction with DCM and separation, the combined extracts were concentrated and purified by ISC012g (0-30%EtOAc Hep) to give 2-Chloro-4-(5-chloro-4-hydroxymethyl-pyridin-3-yl)- benzonitrile (142 mg, 52%) as colorless solid.; ESI-MS m/z: 279 [M+1] Retention time 1.41min. -NMR (CDCI3, 400 MHz) delta 4.66 (s, 2H), 7.53 (d, J= 8.0 Hz, 1H), 7.69 (s, 1H), 7.81 (d, J= 8.0 Hz, 1H), 8.47 (s, 1H), 8.72 (s, 1 H).
  • 12
  • [ 548797-51-9 ]
  • [ 1308669-15-9 ]
  • 13
  • [ 548797-51-9 ]
  • [ 1308669-17-1 ]
  • [ 1308669-16-0 ]
  • 14
  • [ 548797-51-9 ]
  • [ 1308669-43-3 ]
  • 15
  • [ 548797-51-9 ]
  • [ 1255713-79-1 ]
  • [ 1308669-35-3 ]
YieldReaction ConditionsOperation in experiment
9% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere; Step 2: 2-chloro-4-(4-(oxetan-2-yl)pyridin-3-yl)benzonitrile (28) To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzonitrile (569 mg, 2.16 mmol), 3-bromo-4-(oxetan-2-y I) pyridine (462 mg, 2.16 mmol) andPdCI2(dppf).CH2CI2 adduct (176 mg, 0.216 mmol) in DMF(10ml_) was added a solution of Na2C03. (2 M, 2.70 ml, 5.40 mmol) under Nitrogen atomosphare. The mixture was stirred and heated at 100C for4hrs. Reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water and brine. The aqueous layer was extracted with EtOAc. The combined organic phases were dried with Na2S04, filtered and concentrated in vacuo. Purification by ISCOl2g(0-40%EtOAc Heptane) to give 2-chloro-4-(4- (oxetan-2-yl)pyridin-3-yl)benzonitrile (54 mg, 9%) as colorless solid.; ESI-MS mlz: 271[M+1]+, Retention time 1.42min. 1H-NMR (MeOD, 400 MHz) δ 2.58-2.67 (m, 1 H)r 2.82-2.90 (m, 1 H), 4.61-4.67 (m, 1 H), 4.77-4.83 (m, 1 H), 5.88 (t, J = 7.6 Hz, 1 H), 7.46 (dd, J = 8.0, 1.2 Hz, 1 H ), 7.67 (d, J = 1.2 Hz, 1 H), 7.94 (d, J - 8.0 Hz, 1 H), 7.96 (d, J = 4.8 Hz, 1 H), 8.47 (s, 1 H), 8.74 (d, J = 4.8 Hz, 1H); The racemate was separated by chiral HPLC (ChiralPak AS-H, 40%EtOH/Heptane, v/v) to give 28-(enantiomer-1 ) (retention time: 8.58 min) and 28-{enantiomer-2) (retention time. 12.52 min).
  • 16
  • [ 548797-51-9 ]
  • [ 1255713-79-1 ]
  • [ 1308669-37-5 ]
  • [ 1308669-36-4 ]
Historical Records

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[ 548797-51-9 ]

Chlorides

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

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Chemical Structure| 1449475-29-9

[ 1449475-29-9 ]

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.94

Chemical Structure| 445303-10-6

[ 445303-10-6 ]

2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Chemical Structure| 942069-73-0

[ 942069-73-0 ]

2-(3,5-Dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Nitriles

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1449475-29-9

[ 1449475-29-9 ]

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.94

Organoboron

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1449475-29-9

[ 1449475-29-9 ]

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.94

Chemical Structure| 445303-10-6

[ 445303-10-6 ]

2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Chemical Structure| 942069-73-0

[ 942069-73-0 ]

2-(3,5-Dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Aryls

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1449475-29-9

[ 1449475-29-9 ]

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.94

Chemical Structure| 445303-10-6

[ 445303-10-6 ]

2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Chemical Structure| 942069-73-0

[ 942069-73-0 ]

2-(3,5-Dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Organoboron

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1449475-29-9

[ 1449475-29-9 ]

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.94

Chemical Structure| 445303-10-6

[ 445303-10-6 ]

2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Chemical Structure| 942069-73-0

[ 942069-73-0 ]

2-(3,5-Dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Esters

Chemical Structure| 1165935-87-4

[ 1165935-87-4 ]

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.97

Chemical Structure| 1449475-29-9

[ 1449475-29-9 ]

2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Similarity: 0.94

Chemical Structure| 445303-10-6

[ 445303-10-6 ]

2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92

Chemical Structure| 942069-73-0

[ 942069-73-0 ]

2-(3,5-Dichloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.92