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[ CAS No. 443776-94-1 ] {[proInfo.proName]}

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Chemical Structure| 443776-94-1
Chemical Structure| 443776-94-1
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Product Details of [ 443776-94-1 ]

CAS No. :443776-94-1 MDL No. :MFCD11846346
Formula : C13H16BFO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RRKWTJBMMUWQDK-UHFFFAOYSA-N
M.W : 250.07 Pubchem ID :11436620
Synonyms :

Safety of [ 443776-94-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 443776-94-1 ]

* 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 [ 443776-94-1 ]

[ 443776-94-1 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 150-19-6 ]
  • [ 443776-94-1 ]
  • 2-(3'-methoxy)phenoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 16h;
  • 2
  • [ 76-09-5 ]
  • [ 374538-01-9 ]
  • [ 443776-94-1 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran;Molecular sieve; EXAMPLE 20Step 1. 2-Fluoro-5-(4l4l5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzaldehyde. 4-Fluoro-3-formylphenylboronic acid (Lancaster, 3.1 grams, 18 mmol) and pinacol (2.4 grams, 21 mmol) were stirred under nitrogen in anhydrous THF that contained activated 4A molecular sieves. Reaction was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give 4.5 grams of a white solid. 1 H NMR (400 MHz1 CHLOROFORM-d) delta ppm 1.32 (s, 12 H)1 7.14 (dd, J=10.5, 8.3 Hz, 1 H), 8.00 (m, 1 H), 8.31 (dd, J=7.4, 1.6 Hz1 1 H), 10.34 (s, 1 H); MS(APCI+) m/z 251 (MH+).
With magnesium sulfate; In methanol; at 20℃; for 6h; General procedure: To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75-77 C) in88% yield (513 mg). 1H-NMR (CD3OD-d4) delta ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) delta ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;11B-NMR (CDCl3) delta ppm 34.82.
  • 3
  • [ 2759-28-6 ]
  • [ 443776-94-1 ]
  • 2-[4-(benzyl)piperazin-1'-yl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 16h;
  • 4
  • [ 873-62-1 ]
  • [ 443776-94-1 ]
  • 3-[2-formyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxy]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 16h;
  • 5
  • [ 831-82-3 ]
  • [ 443776-94-1 ]
  • 2-(4'-phenoxy)phenoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 16h;
  • 6
  • [ 57260-71-6 ]
  • [ 443776-94-1 ]
  • 2-[4-(tert-butoxycarbonyl)piperazin-1'-yl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 16h;
  • 7
  • [ 443776-94-1 ]
  • [ 108-95-2 ]
  • [ 364354-24-5 ]
YieldReaction ConditionsOperation in experiment
64% With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 16h;
  • 8
  • [ 20938-74-3 ]
  • [ 443776-94-1 ]
  • 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[<i>b</i>]thiophene-2-carboxylic acid methylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 140℃; for 0.5h; microwave irradiation;
  • 9
  • [ 7383-61-1 ]
  • [ 443776-94-1 ]
  • 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[<i>b</i>]thiophene-2-carboxylic acid isopropyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 140℃; for 0.5h; microwave irradiation;
  • 10
  • [ 4822-44-0 ]
  • [ 443776-94-1 ]
  • 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[<i>b</i>]thiophene-2-carboxylic acid phenylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 140℃; for 0.5h; microwave irradiation;
  • 11
  • [ 68-11-1 ]
  • [ 443776-94-1 ]
  • 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[<i>b</i>]thiophene-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In ethanol; acetonitrile at 140℃; for 1h; microwave irradiation;
  • 12
  • [ 623-51-8 ]
  • [ 443776-94-1 ]
  • [ 889860-69-9 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In acetonitrile at 140℃; for 0.5h; microwave irradiation;
  • 13
  • [ 93777-26-5 ]
  • [ 73183-34-3 ]
  • [ 443776-94-1 ]
YieldReaction ConditionsOperation in experiment
82% With potassium acetate; dimethyl sulfoxide at 80℃;
  • 14
  • [ 1001200-45-8 ]
  • [ 443776-94-1 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 3-dibromomethyl-4-fluorobenzeneboronic acid pinacol ester With pyridine at 100℃; for 1.5h; Stage #2: With water Further stages.;
  • 15
  • [ 443776-94-1 ]
  • 5-(2-aminoquinazolin-6-yl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile; ethanol / 1 h / 140 °C / microwave irradiation 2: 0.061 g / K2CO3 / Pd(dppf)Cl2 / acetonitrile; H2O; ethanol / 1 h / 95 °C / microwave irradiation
  • 16
  • [ 443776-94-1 ]
  • ethyl 5-(2-aminoquinazolin-6-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / K2CO3 / acetonitrile / 0.5 h / 140 °C / microwave irradiation 2: 0.123 g / K2CO3 / Pd(dppf)Cl2 / acetonitrile; H2O / 0.5 h / 90 °C / microwave irradiation
  • 17
  • [ 443776-94-1 ]
  • 5-(2-aminoquinazolin-6-yl)-N-methylbenzo[b]thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 0.5 h / 140 °C / microwave irradiation 2: 0.038 g / K2CO3 / Pd(dppf)Cl2 / acetonitrile; H2O / 1.5 h / 95 °C / microwave irradiation
  • 18
  • [ 443776-94-1 ]
  • isopropyl 5-(2-aminoquinazolin-6-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 0.5 h / 140 °C / microwave irradiation 2: 0.145 g / K2CO3 / Pd(dppf)Cl2 / acetonitrile; H2O / 1 h / 90 °C / microwave irradiation
  • 19
  • [ 443776-94-1 ]
  • 5-(2-aminoquinazolin-6-yl)-N-phenylbenzo[b]thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 0.5 h / 140 °C / microwave irradiation 2: 0.109 g / K2CO3 / Pd(dppf)Cl2 / acetonitrile; H2O / 1.5 h / 90 °C / microwave irradiation
  • 20
  • [ 443776-94-1 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / N,N-dimethyl-acetamide / 16 h / 110 °C 2: 61 percent / K2CO3 / trans-di-μ-acetobis[2-(di-o-tolylphosphino)benzyl]Pd(II)2 / various solvent(s) / 16 h / 130 °C
  • 21
  • [ 443776-94-1 ]
  • 2-phenoxy-5-phenylbenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / N,N-dimethyl-acetamide / 16 h / 110 °C 2: 83 percent / aq. Na2CO3 / Pd(PPh3)4 / toluene; ethanol / 2.5 h / 80 °C
  • 22
  • [ 141-91-3 ]
  • [ 443776-94-1 ]
  • 2-(2,6-dimethyl-morpholin-4-yl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 105℃; Heating / reflux; 20.2 Step 2. 2-(2,6-Dimethyl-morpholin-4-yl)-5-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-benzaldehyde. 2-Fluoro-5-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaboro.an-2-yl)-benzaldehyde (4.6 grams, 18 mmol) and potassium carbonate (3.8 grams, 27 mmol) were suspended in DMF (3 ml_). Dimethyl morpholine (2.6 ml_, 21 mmol) was then added and mixture was heated overnight at 105 0C. Reaction mixture was cooled and filtered to remove salts. The dropwise addition of water induced formation of a precipitate. The yellow precipitate was filtered off and collected. Dried in vacuum oven to obtain 4.26 grams of desired product. 1 H NMR (400 MHz,CHLOROFORM-d) δ ppm 1.21 (d, J=6.1 Hz, 6 H), 1.32 (s, 12 H), 2.65 (m, 2 H), 3.16 (d, J=11.5 Hz1 2 H), 3.93 (m, 2 H), 7.03 (d, J=8.3 Hz, 1 H), 7.90 (dd, J=8.2, 1.6 Hz, 1 H), 8.22 (d, J=1.5 Hz, 1 H), 10.17 (s, 1 H); MS(APCI+) m/z 346 (MH+).
  • 23
  • [ 443776-94-1 ]
  • [ 1544673-57-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / 5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 72 h / 20 °C
  • 24
  • [ 443776-94-1 ]
  • [ 1544673-73-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / 5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 72 h / 20 °C 4: hydrazine hydrate / tetrahydrofuran / 12 h / Reflux
  • 25
  • [ 443776-94-1 ]
  • [ 1352733-99-3 ]
YieldReaction ConditionsOperation in experiment
312 mg With sodium tetrahydroborate at 20℃; for 5h; [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (2a). General procedure: To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75-77 °C) in88% yield (513 mg). 1H-NMR (CD3OD-d4) δ ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) δ ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;11B-NMR (CDCl3) δ ppm 34.82.
  • 26
  • [ 443776-94-1 ]
  • C14H20BFO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere
  • 27
  • [ 867256-77-7 ]
  • [ 7188-38-7 ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • N-(2-(tert-butylamino)-1-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxoethyl)-2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline; 2-fluoro-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde In methanol at 60℃; for 1h; Microwave irradiation; Stage #2: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid; tert-butylisonitrile In methanol at 60℃; for 2h; Microwave irradiation; General procedure for synthesis of multiple boron-containing Ugi analogs General procedure: N-(2-(tert-Butylamino)-2-oxo-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide (1) A 10-mL glass tube containing 4-aminophenylboronic acid pinacol ester (300 mg, 1.37 mmol), 4-formylphenylboronic acid pinacol ester (256 mg, 1.09 mmol), and 2.7 mL methanol was first stirred for 60 min under microwave irradiation (50 °C, 150 W). Then, 4-carboxyphenylboronic acid pinacol ester (374 mg, 1.51 mmol) and tert-butyl isocyanide (0.2 mL, 1.37 mmol) were added to the reaction mixture. Microwave irradiation was applied again for an additional 120 min (50 °C, 150 W) under medium-speed magnetic stirring, and the reaction mixture was concentrated and redissolved in ethylacetate. The crude solution was then washed with 1 M HCl(aq) and NaHCO3(aq), respectively. The organic solution was collected and dried over MgSO4 and concentratedin vacuo. The resulting crude material was purified by flash chromatography with ethyl acetate:n-hexane = 3:7 to afford the desired product in 85 %yield (708.19 mg).
  • 28
  • [ 7188-38-7 ]
  • [ 180516-87-4 ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • N-(2-(tert-butylamino)-1-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxoethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline; 2-fluoro-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde In methanol at 60℃; for 1h; Microwave irradiation; Stage #2: tert-butylisonitrile; 4-carboxyphenylboronic acid pinacol ester In methanol at 60℃; for 2h; Microwave irradiation; General procedure for synthesis of multiple boron-containing Ugi analogs General procedure: N-(2-(tert-Butylamino)-2-oxo-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide (1) A 10-mL glass tube containing 4-aminophenylboronic acid pinacol ester (300 mg, 1.37 mmol), 4-formylphenylboronic acid pinacol ester (256 mg, 1.09 mmol), and 2.7 mL methanol was first stirred for 60 min under microwave irradiation (50 °C, 150 W). Then, 4-carboxyphenylboronic acid pinacol ester (374 mg, 1.51 mmol) and tert-butyl isocyanide (0.2 mL, 1.37 mmol) were added to the reaction mixture. Microwave irradiation was applied again for an additional 120 min (50 °C, 150 W) under medium-speed magnetic stirring, and the reaction mixture was concentrated and redissolved in ethylacetate. The crude solution was then washed with 1 M HCl(aq) and NaHCO3(aq), respectively. The organic solution was collected and dried over MgSO4 and concentratedin vacuo. The resulting crude material was purified by flash chromatography with ethyl acetate:n-hexane = 3:7 to afford the desired product in 85 %yield (708.19 mg).
  • 29
  • [ 269409-73-6 ]
  • [ 119072-55-8 ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • N-(2-(tert-butylamino)-1-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxoethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% General procedure: N-(2-(tert-Butylamino)-2-oxo-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide (1) A 10-mL glass tube containing 4-aminophenylboronic acid pinacol ester (300 mg, 1.37 mmol), 4-formylphenylboronic acid pinacol ester (256 mg, 1.09 mmol), and 2.7 mL methanol was first stirred for 60 min under microwave irradiation (50 C, 150 W). Then, 4-carboxyphenylboronic acid pinacol ester (374 mg, 1.51 mmol) and tert-butyl isocyanide (0.2 mL, 1.37 mmol) were added to the reaction mixture. Microwave irradiation was applied again for an additional 120 min (50 C, 150 W) under medium-speed magnetic stirring, and the reaction mixture was concentrated and redissolved in ethylacetate. The crude solution was then washed with 1 M HCl(aq) and NaHCO3(aq), respectively. The organic solution was collected and dried over MgSO4 and concentratedin vacuo. The resulting crude material was purified by flash chromatography with ethyl acetate:n-hexane = 3:7 to afford the desired product in 85 %yield (708.19 mg).
  • 30
  • [ 626-55-1 ]
  • [ 443776-94-1 ]
  • 2-fluoro-5-(pyridin-3-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;
  • 31
  • [ 443776-94-1 ]
  • 3-(4-fluoro-3-vinylphenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 12 h / 80 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / diethyl ether / Inert atmosphere; Schlenk technique 2.2: 2 h / 20 °C
  • 32
  • [ 443776-94-1 ]
  • 2-(4-fluoro-3-vinylphenyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 12 h / 80 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / diethyl ether / Inert atmosphere; Schlenk technique 2.2: 2 h / 20 °C
  • 33
  • [ 443776-94-1 ]
  • 1-methyl-2-(pyridin-2-yl)-6-(pyridin-3-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 12 h / 80 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / diethyl ether / Inert atmosphere; Schlenk technique 2.2: 2 h / 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 12 h / 20 - 50 °C / Glovebox; Inert atmosphere
  • 34
  • [ 443776-94-1 ]
  • 1-methyl-2-(pyridin-2-yl)-6-(thiophen-2-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 12 h / 80 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / diethyl ether / Inert atmosphere; Schlenk technique 2.2: 2 h / 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 12 h / 20 - 50 °C / Glovebox; Inert atmosphere
  • 35
  • [ 1003-09-4 ]
  • [ 443776-94-1 ]
  • 2-fluoro-5-(thiophen-2-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;
  • 36
  • [ 867256-77-7 ]
  • 2-(3-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • 2-fluoro-N-(1-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxo-2-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)amino)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 2-(4-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde In 2,2,2-trifluoroethanol at 65℃; for 0.25h; Microwave irradiation; Stage #2: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid; 2-(3-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In 2,2,2-trifluoroethanol at 65℃; for 2h; Microwave irradiation;
  • 37
  • [ 867256-77-7 ]
  • 2-(4-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • 2-fluoro-N-(1-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxo-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)amino)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 2-(4-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde In 2,2,2-trifluoroethanol at 65℃; for 0.25h; Microwave irradiation; Stage #2: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid; 2-(4-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In 2,2,2-trifluoroethanol at 65℃; for 2h; Microwave irradiation;
  • 38
  • [ 867256-77-7 ]
  • 2-(3-fluoro-4-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • 2-fluoro-N-(2-((2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)amino)-1-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxoethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: 2-(4-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde In 2,2,2-trifluoroethanol at 65℃; for 0.25h; Microwave irradiation; Stage #2: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid; 2-(3-fluoro-4-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In 2,2,2-trifluoroethanol at 65℃; for 2h; Microwave irradiation;
  • 39
  • [ 867256-77-7 ]
  • 2-(3-fluoro-4-(isocyanomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 214360-73-3 ]
  • [ 443776-94-1 ]
  • (4-(4-borono-N-(2-((4-borono-2-fluorobenzyl)amino)-1-(5-borono-2-fluorophenyl)-2-oxoethyl)-2-fluorobenzamido)phenyl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 2,2,2-trifluoroethanol / 0.25 h / 65 °C / Microwave irradiation 1.2: 2 h / 65 °C / Microwave irradiation 2.1: sodium (meta)periodate / tetrahydrofuran; lithium hydroxide monohydrate / 0.5 h / 45 °C / Microwave irradiation 2.2: 8 h
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