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[ CAS No. 261621-12-9 ]

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Chemical Structure| 261621-12-9
Chemical Structure| 261621-12-9
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Product Details of [ 261621-12-9 ]

CAS No. :261621-12-9 MDL No. :MFCD03701505
Formula : C12H21BO3Si Boiling Point : 330.3°C at N/A mmHg
Linear Structure Formula :- InChI Key :-
M.W :252.19 g/mol Pubchem ID :-
Synonyms :

Safety of [ 261621-12-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P405-P305+P351+P338-P304+P340-P280 UN#:N/A
Hazard Statements:H335-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 261621-12-9 ]

  • Downstream synthetic route of [ 261621-12-9 ]

[ 261621-12-9 ] Synthesis Path-Downstream   1~26

  • 1
  • methyl 3-bromobicyclo[2.2.2]octa-2,5-diene-2-carboxylate [ No CAS ]
  • [ 261621-12-9 ]
  • methyl 3-[3-(tert-butyldimethylsilyloxy)phenyl]bicyclo[2.2.2]octa-2,5-diene-2-carboxylate [ No CAS ]
  • 2
  • [ 121-43-7 ]
  • [ 65423-56-5 ]
  • [ 261621-12-9 ]
  • 3
  • [ 61294-07-3 ]
  • [ 261621-12-9 ]
  • 1-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-phenyl]-3-(3-trifluoromethyl-phenylimino)-1,3-dihydro-indol-2-one [ No CAS ]
  • 4
  • [ 261621-12-9 ]
  • 7-[3-(tert-butyldimethylsilyloxy)phenyl]-6-hydroxymethyl-1,3,3a,4,5,6-hexahydro-1-isobenzofuranone [ No CAS ]
  • 5
  • [ 261621-12-9 ]
  • methyl 3-[3-(tert-butyldimethylsilyloxy)phenyl]-5,6-dihydroxy-bicyclo[2.2.2]oct-2-ene-2-carboxylate [ No CAS ]
  • 6
  • [ 61294-07-3 ]
  • [ 261621-12-9 ]
  • [ 903878-25-1 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine;copper diacetate; In dichloromethane; at 20℃; A mixture of 3-[3-(Trifluoromethyl)phenyl]azamethylene}-1H-benzo[d]azolin-2-one (3.19 g, 0.011 mol), 3-(TBDMS-O)-phenylboronic acid (2.78 g, 0.013 mol), and Cu(OAc)2 (1.79 g, 0.012 mmol) in CH2Cl2 (300 mL) was stirred at rt for 5 min. TEA (4.59 mL) was added dropwise. The reaction was stirred at rt overnight. The reaction was diluted with CH2Cl2 and washed with saturated EDTA solution (2×) and water. After drying over Na2SO4, the organic solvent was removed in vacuo. The crude product was purified by silica gel chromatography, eluting with CHCl3/2M NH3 in MeOH (49:1), giving the desired product (3.36 g, 62% yield). ESMS m/e: 497 (M+H)+.
62% With copper diacetate; triethylamine; In dichloromethane; at 20℃; A mixture of 3-[3-(trifluoromethyl)phenyl]azamethylene}-1H-benzo[d]azolin-2-one (3.19 g, 0.011 mol), 3-(TBDMS-O)-phenylboronic acid (2.78 g, 0.013 mol), and Cu(OAc)2 (1.79 g, 0.012 mmol) in CH2Cl2 (300 mL) was stirred at rt for 5 min. TEA (4.59 mL) was added dropwise. The reaction was stirred at rt overnight. The reaction was diluted with CH2Cl2 and washed with saturated EDTA solution (2×) and water. After drying over Na2SO4, the organic solvent was removed in vacuo. The crude product was purified by silica gel chromatography, eluting with CHCl3/2 M NH3 in MeOH (49:1), giving the desired product (3.36 g, 62% yield). ESMS m/e: 497 (M+H)+.
  • 7
  • [ 57848-46-1 ]
  • [ 261621-12-9 ]
  • 3'-(tert-butyldimethylsilyloxy)-3-fluoro-1,1'-biphenyl-4-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Suzuki coupling of commercially available 4-bromo-2-fiuoro- benzaldehyde (109B) with commercially available 3-(tert- butyldimethylsilyoxy)phenylboronic acid (123B) gives 3'-( tert-butyldimethylsilyoxy)-3- fluoro-l,r-biphenyl-4-carbaldehyde (124B). Treatment of 124B with 2-(trimethylsilyl) ethanethiol in the presence of potassium carbonate in dimethylformamide produces a solution of thiophenol derivative 125B that is treated directly with 49B to produce 126aB. Condensation of 126aB with aniline gives the corresponding imine 126bB. In the next step, 3bB was treated with titanium tetrachloride and N-ethyldiisopropyl-amine followed by treatment with 126bB to effect enantiospecific condensation to provide 127B. Treatment of 127B with excess N,0-bistrimethylsilyl-acetamide followed by a catalytic amount of tetrabutylammonium fluoride hydrate results in ring closure to the desired beta-lactam (128B). Oxidation of 128B with oxone results in the formation of sulfone 129B. Removal of the benzyl groups is done by hydrogenolysis of 129B over Pearlman's catalyst to give 130B. Protection of the 4",6"-hydroxyls of 130B as ap- methoxybenzylidene followed by exhaustive acylation with chloroacetic anhydride to give the fully protected derivative 131B. The benzylidene is then cleaved with acid to give diol 132B. The diol 132B is then reacted with 2-fluorophenyl iso-cyanate with copper (I) catalysis to give 133B. The chloroacetates are removed by treatment with EPO <DP n="313"/>sodium methoxide in methanol to give 134B, which is treated with aqueous HF to provide 135B.
  • 8
  • [ 110-71-4 ]
  • [ 275386-74-8 ]
  • [ 497-19-8 ]
  • [ 261621-12-9 ]
  • (Z)-1,3-Dihydro-5-fluoro-4-(3-hydroxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
(Ph3P)2PdCl2; In N,N-dimethyl-formamide; Example 61 (Z)-1,3-Dihydro-5-fluoro-4-(3-hydroxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (HHH) 3-tert-Butyl-dimethyl-silyloxy-phenylboronic acid was prepared according to the procedure for preparing 4-tert-butyl-dimethyl-silyloxy-phenylboronic acid of: S. Yonezawa et al., Total Synthesis of Terprenin, a Novel Immunosuppressive p-Terphenyl Derivative. J. Org. Chem. 1998, 63,5831-5837. A solution of (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (50 mg, 0.135 mmol) (Starting Material 11), 2M aqueous Na2CO3 solution (0.14 mL), (Ph3P)2PdCl2 (11 mg, 0.0135 mmol) and 3-tert-butyl-dimethyl-silyloxy-phenylboronic acid (0.14 g, 0.54 mmol) in 5 ml of a 1:4 mixture of DMF:1,2-dimethoxyethane (5 mL) was heated at 104 C. for 3 days. The reaction mixture was concentrated and the crude material was washed with methanol to give (Z)-1,3-Dihydro-5-fluoro-4-(3-hydroxyphenyl)-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one. (Yield 10 mg, 22%).
  • 9
  • [ 100-76-5 ]
  • [ 1189-71-5 ]
  • [ 1044409-49-5 ]
  • [ 2039-82-9 ]
  • [ 100306-34-1 ]
  • [ 261621-12-9 ]
  • trans-1,2-cyclohexanediamine [ No CAS ]
  • 1-[4-(4-{(2S,3R)-2-(3'-hydroxybiphenyl-4-yl)-3-[(3S)3-hydroxy-3-phenylpropyl]-4-oxoazetidin-1-yl}phenyl)butyl]-1-azoniabicyclo[2.2.2]octane chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen fluoride; potassium carbonate;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); A quaternary salt is made in the following manner. (3-[tert- butyl(dimethyl)silyl]oxy}phenyl)boronic acid and 4-bromostyrene are coupled under Suzuki conditions with tetrakis(triphenylphosphine)palladium(0) and 2.0 M aqueous potassium carbonate in toluene-ethanol solvent. The product is reacted with chlorosulfonyl isocyanate in ethereal solvent followed by alkali aqueous work-up to generate a beta-lactam. The amide proton is exchanged for an aryl group by reaction with 4-iodophenylcarbonylallyl (generated from the commercially available acid by borane reduction and protected with allyl chloroformate) using trans- 1,2- cyclohexanediamine and copper (T) iodide in decane-dioxane as solvent. Deprotonation of the 3-position of the beta-lactam with a suitable base, such as lithium diisopropylamide, and subsequent quenching with tert-butyl[(lS)-4-iodo-l- phenylbutyl]oxy}dimethylsilane (generated from the commercially available (S)-(-)-3- chloro-1 -phenyl- 1-propanol by protection with tert-butyldimethylchlorosilane and Finkelstein reaction with sodium iodide) provide the 3-substituted intermediate. The allyloxycarbonate protecting group is removed with ammonium formate and tetrakis(triphenylphosphine)palladium(0) in tetrahydrofuran and the resulting alcohol converted into the bromide using carbon tetrabromide and triphenylphosphine in dichloromethane. The silyl protecting groups are removed from the benzyl alcohol EPO <DP n="234"/>and the phenol using 48% hydrofluoric acid in acetonitrile. The resulting compound is reacted with a tertiary amine, such as quinuclidine, purified by HPLC and passed through a chloride ion-exchange column to afford l-[4-(4-{(2S,3R)-2-(3'- hydroxybiphenyl-4-yl)-3 - [(3 S)-3 -hydroxy-3 -phenylpropyl] -4-oxoazetidin- 1 - yl}phenyl)butyl]- 1 -azoniabicyclo[2.2.2]octane chloride.
  • 10
  • [ 20028-68-6 ]
  • [ 261621-12-9 ]
  • [ 915693-38-8 ]
  • 11
  • [ 875103-67-6 ]
  • [ 261621-12-9 ]
  • C31H36N4O2 [ No CAS ]
  • C37H50N4O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; 2.7 g (5.71 mmol) of XI, 1.73 g (6.85 mrnol) of 3-(tert-butyldimethyl-silyl-oxy)phenylboronic acid, 3.63 g (34.25 mmol) of Na2COs and 0.198 g of tetrakis(diphenylphosphine)paliadium are dissolved in a mixture of 85 ml of 1 ,2-dimethoxyethane and 1 3 ml of water.The reaction mixture is refluxed for 8 hours. It is then diluted in ethyl acetate and water is added. The organic phase is washed with water and then dried over Na2SO4, and the product is evaporated to dryness.After flash chromatography on silica gel, eluting with 1/1 EtOAc/CH2Cl2and then 80/20 CH2CI2/MeOH, 1.08 g of silyl product are obtained in the formof an oil, and 375 mg of desilylated product are also obtained.1 H NMR silyl product:(DMSO-d6): 0.00 (6H, s); 0.74 (9H, s); 0.87-1.80 (18H, m); 4.00-4.20 (4H, m); 6.48-6.58 (1H, m); 6.86-7.20 (6H, m); 7.45-7.52 (1H, m); 7.74 (1H, s); 7.97-8.29 (4H, m).1H NMR deprotected product:(DMSO-d6); 0.80-1.85 (18H, m); 4.00-4.20 (4H, m); 6.40-6.47 (1H, m); 6.85-7.10 (6H, m); 7.45-7.52 (1H, m); 7.66 (1H, s); 7.97-8.29 (4H, m); 9.17 (1H, s).
  • 12
  • [ 104-92-7 ]
  • [ 261621-12-9 ]
  • [ 1096698-52-0 ]
  • 13
  • [ 603125-59-3 ]
  • [ 261621-12-9 ]
  • [ 603122-32-3 ]
  • 14
  • [ 121489-29-0 ]
  • [ 261621-12-9 ]
  • [ 603122-01-6 ]
  • 15
  • [ 261621-12-9 ]
  • [ 16234-15-4 ]
  • [ 885616-90-0 ]
  • 16
  • [ 98141-42-5 ]
  • [ 261621-12-9 ]
  • [ 1292902-28-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 100℃; for 20h;Inert atmosphere; The following are combined under argon:210.9 mg of ?2?, 372.36 mg of 3-(tert-butylmethylsilyloxy)phenylboronic acid, 52.45 mg of tetrakis(triphenylphosphine)palladium(0), 68.02 mg of potassium carbonate, 6 ml of toluene. The mixture is stirred at 100 for 20h. The mixture is subjected to conventional work-up and purified over an RP column, giving 155 mg of ?3?.
  • 17
  • (Sp)-12-bromo[2.2]paracyclophan-4-yl trifluoromethanesulfonate [ No CAS ]
  • [ 4559-70-0 ]
  • [ 261621-12-9 ]
  • (Sp)-{12-(3-tert-butyldimethylsiloxyphenyl)[2.2]paracyclophan-4-yl}diphenylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% (Sp)-{12-(3-tert-Butyldimethylsiloxyphenyl)[2.2]paracyclophan-4-yl}diphenylphosphine oxide [(Sp)-2a]. To a solution of (Sp)-1 (206 mg, 0.473 mmol), Ph2P(O)H (191 mg, 0.946 mmol), Pd(OAc)2 (5.3 mg, 0.024 mmol) and dppf (21.0 mg, 0.0378 mmol) in DMSO (4.7 mL) was added i-Pr2NEt (0.25 mL, 1.4 mmol) at room temperature under an argon atmosphere. After being stirred for 12 h at 100 C, the reaction mixture was cooled, quenched by addition of 10% aqueous HCl, and extracted with EtOAc. The extract was washed with water and brine, dried and concentrated to dryness. The residue was chromatographed with hexane-EtOAc (5:1) to afford a 2.9:1 mixture of the bromocyclophanylphosphine oxide1 and the trifluoromethanesulfonyloxycyclophanylphosphine oxide1 (139 mg, 58%) as a colorless solid. A solution of the phosphine oxide (139 mg, 0.275 mmol), 3-(tert-butyldimethylsiloxy)phenylboronic acid (160 mg, 0634 mmol), PdCl2(dppf) (22.6 mg, 0.0277 mmol), and K3PO4 (175 mg, 0.825 mmol) in toluene (3.0 mL) was stirred for 20 h at 100 C under an argon atmosphere. Then the reaction mixture was cooled and concentrated to dryness. The residue was chromatographed with hexane-EtOAc (5:1) to afford (Sp)-2a (51.4 mg, 30%) along with the recovered phosphine oxide-bromide (21.0 mg, 21% recovery) and phosphine oxide-triflate (39.8 mg, 100%). (Sp)-2a: A colorless solid: mp 95-97 C; [α]D 26 +9.2 (c 1.00, CHCl3); IR νmax/cm-1 1180; 1H NMR (400 MHz) δ 7.85-7.81 (m, 2H), 7.69-7.65 (m, 2H), 7.50-7.35 (m, 7H), 7.16 (t, J =7.8 Hz, 1H), 7.12 (s, 1H), 6.88 (s, 1H), 6.75-6.68 (m, 4H), 6.62-6.59 (m, 2H), 3.67 (dd, J = 13.3, 9.2 Hz, 1H), 3.45-3.37 (m, 1H), 3.30 (t, J = 10.5 Hz, 1H), 3.05 (t, J = 10.5 Hz, 2H), 2.92-2.69 (m, 3H), 2.14 (dt, J = 13.3, 8.7 Hz, 1H), 0.98 (s, 9H), 0.18 (d, J = 8.2 Hz, 6H); 13C NMR (100 MHz) δ 155.2, 145.9 (d, JC-P = 7.7 Hz), 141.9, 140.8, 140.0, 139.4 (d, JC-P = 12.5 Hz), 136.9 (d, JC-P = 2.9 Hz), 136.3, 136.2 (d, JC-P = 102.6 Hz), 135.6 (d, JC-P = 11.5 Hz), 135.2, 134.0 (d, JC-P = 12.5 Hz), 133.4, 132.2, (d, JC-P = 101.6 Hz), 132.2 (d, JC-P = 8.6 Hz), 131.4 (d, JC-P = 2.9 Hz), 131.2 (d, JC-P = 2.9 Hz), 131.1, 130.9 (d, JC-P = 9.6 Hz), 129.4, 128.7 (d, JC-P = 105.5 Hz), 128.3 (d, JC-P = 11.6 Hz), 128.2 (d, JC-P = 9.6 Hz), 122.1, 121.5, 118.5, 36.0 (d, JC-P = 4.8 Hz), 35.3, 34.9, 33.3, 25.7, 18.2, -4.32, -4.40; 31P NMR (242 MHz) δ +24.15; MS (EI) m/z 614 (M+, 100.0); HRMS calcd for C40H43SiO2P 614.2770, found 614.2771.
  • 18
  • [ 261621-12-9 ]
  • {12-(3-hydroxyphenyl)[2.2]paracyclophan-4-yl}diphenylphosphine [ No CAS ]
  • 19
  • [ 261621-12-9 ]
  • C34H29O2P [ No CAS ]
  • 20
  • [ 261621-12-9 ]
  • [ 2873-29-2 ]
  • [ 1453855-64-5 ]
YieldReaction ConditionsOperation in experiment
47% With palladium diacetate; In acetonitrile; at 20℃; To a solution of [(2R,3S,4R)-3,4-diacetoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate (1.100 g, 4.040 mmol) in 10 mL of acetonitrile are added [3-(tert-butyl-dimethyl- silyl)oxyphenyl]boronic acid (2.038 g, 8.080 mmol) and Pd(OAc)2 (136.1 mg, 0.6060 mmol). The mixture is stirred at rt for 5 h and then to it are added another batch of Pd(OAc)2 (136 mg, 0.606 mmol) and [3-(tert-butyl-dimethyl-silyl)oxyphenyl]boronic acid (2.038 g, 8.080 mmol). It is then stirred at rt overnight. The mixture is diluted with 20 mL of CH2CI2 and filtered over a pad of celite. The filtrate is concentrated and the residue is separated on Biotage SNAP lOOg silica gel cartridge using a gradient of Hex/EtOAc (0-20%) in 20 column volume to afford the title compound (805 mg, 1.91 mmol, 47%) as an oil, which solidifies upon standing. XH NMR (CDCI3, 400 MHz): 7.06 (m, 1H), 6.78 (m, 1H), 6.70 (m, 1H), 6.60 (m, 1H), 5.97 (m, 1H), 5.71 (m, 1H), 5.09 (m, 2H), 4.08 (m, 1H), 3.85 (m, 1H), 3.62 (m, 1H), 1.88 and 1.87 (2s, 6H), 0.78 (m, 9H), 0.00 (m, 6H).
47% With palladium diacetate; In acetonitrile; at 20℃; Step I: [(2R,3S,6S)-3-Acetoxy-6-[3-[ter/-butyl(dimethyl)silyl]oxyphenyl]-3,6-dihydro-2H- pyran-2-yl]methyl acetate To a solution of [(2R,3S,4R)-3,4-diacetoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate (1.100 g, 4.040 mmol) in 10 mL of CH3CN are added [3-(tert-butyl-dimethyl- silyl)oxyphenyl]boronic acid (2.038 g, 8.080 mmol) and Pd(OAc)2 (136.1 mg, 0.6060 mmol). The mixture is stirred at RT for 5 h and then to it are added another batch of Pd(OAc)2 (136 mg, 0.606 mmol) and [3-(/er/-butyl-dimethyl-silyl)oxyphenyl]boronic acid (2.038 g, 8.080 mmol). It is then stirred at RT overnight. The mixture is diluted with 20 mL of CH2CI2 and filtered over a pad of celite. The filtrate is concentrated and the residue is separated on Biotage SNAP lOOg silica gel cartridge using a gradient of EtO Ac in Hex (0-20%) in 20 column volume to afford the title product (805 mg, 47%) as an oil, which solidifies upon standing. XH NMR (CDC13, 400 MHz): 7.06 (m, 1H), 6.78 (m, 1H), 6.70 (m, 1H), 6.60 (m, 1H), 5.97 (m, 1H), 5.71 (m, 1H), 5.09 (m, 2H), 4.08 (m, 1H), 3.85 (m, 1H), 3.62 (m, 1H), 1.88 and 1.87 (2s, 6H), 0.78 (m, 9H), 0.00 (m, 6H).
  • 21
  • [ 261621-12-9 ]
  • [ 1453855-65-6 ]
  • 22
  • [ 261621-12-9 ]
  • [ 1453855-49-6 ]
  • 23
  • [ 261621-12-9 ]
  • [ 1453855-79-2 ]
  • 24
  • [ 261621-12-9 ]
  • [ 1453851-77-8 ]
  • 25
  • [ 261621-12-9 ]
  • [ 1453855-80-5 ]
  • 26
  • [ 261621-12-9 ]
  • [ 1453855-81-6 ]
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