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[ CAS No. 913835-67-3 ]

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Chemical Structure| 913835-67-3
Chemical Structure| 913835-67-3
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Product Details of [ 913835-67-3 ]

CAS No. :913835-67-3 MDL No. :MFCD08436056
Formula : C14H15BN2O4 Boiling Point : 509.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :286.09 g/mol Pubchem ID :-
Synonyms :

Safety of [ 913835-67-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P304+P340-P405-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H319-H315-H302-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 913835-67-3 ]

  • Downstream synthetic route of [ 913835-67-3 ]

[ 913835-67-3 ] Synthesis Path-Downstream   1~14

  • 3
  • [ 913835-67-3 ]
  • [ 889676-34-0 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-(Bromomethyl)-3-fluorobenzene; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 18h;
  • 4
  • [ 913835-67-3 ]
  • [ 456-41-7 ]
  • [ 889676-34-0 ]
  • [ 1227625-69-5 ]
YieldReaction ConditionsOperation in experiment
With trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); sodium carbonate In tetrahydrofuran at 60℃; for 2h;
  • 5
  • [ 913835-67-3 ]
  • [ 456-41-7 ]
  • [ 1227625-69-5 ]
YieldReaction ConditionsOperation in experiment
60% With trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); sodium carbonate In tetrahydrofuran at 60℃; for 1h;
  • 6
  • [ 913835-67-3 ]
  • [ 1207731-18-7 ]
  • [ 1207731-19-8 ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 1.5h; Inert atmosphere; Reflux;
  • 7
  • [ 104-92-7 ]
  • [ 913835-67-3 ]
  • [ 1207731-35-8 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 4h; Inert atmosphere;
  • 8
  • [ 913835-67-3 ]
  • [ 623-00-7 ]
  • [ 1186403-09-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 4h; Inert atmosphere;
  • 9
  • [ 913835-67-3 ]
  • 7-bromo-2-cyanoimidazo[1,2-a]pyridine [ No CAS ]
  • [ 1428267-33-7 ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 80℃; for 2h; N-Boc-6-cyano-2-(2-cyanoimidazo[l,2-a]pyridin-7-yl)indole To a 50 mL round bottom flask was added Ar-Boc-6-cyanoindol-2-ylboronic acid (700 mg, 2.45 mmol), 7-bromoimidazo[l,2-a]pyridine-2-carbonitrile (272 mg, 1.22 mmol), Pd(Ph3P)4 (141 mg, 0.12 mmol), Na2C03 (1M, 7.3 mL), toluene (24.0 mL) and EtOH (12.0 mL). The resulting brown mixture turned black upon heating to 80°C. The reaction mixture was stirred at this temperature for 2 hours and cooled to room temperature. The organic layer was separated and the aqueous was extracted with EtOAc (2 x 20 mL). The combined organics were dried over anhydrous Na2S04, filtered, and evaporated to yield yellow residue, which was purified by column chromatography on silica gel (hex/EtOAc) to provide 246 mg (53%) of product as a yellow solid: Rf: 0.42 (1 : 1 hex:EtOAc); ¾ NMR (300 MHz, CDC13): 8.51 (s, 1H), 8.17 (dd, 1H), 8.09 (d, 1H), 7.74 (s, 1H), 7.69 (d, 1H), 7.56 (dd, 1H), 7.03 (dd, 1H), 6.78 (s, 1H), 1.48 (s, 9H).
  • 10
  • [ 913835-67-3 ]
  • [ 1216121-34-4 ]
  • [ 1428267-39-3 ]
YieldReaction ConditionsOperation in experiment
39% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 80℃; for 2h; To a 50 mL round bottom flask was added boronic acid 1 (417 mg, 1.46 mmol), bromide 3 (270 mg, 1.21 mmol), Pd(Ph3P)4 (140 mg, 0.12 mmol), Na2C03 (lM, 7.3 mL), toluene (24.0 mL) and EtOH (12.0 mL). The resultant brown mixture turned black upon heating to 80°C. The reaction mixture was stirred at this temperature for 2 hours and cooled to room temperature. The organic layer was separated and the aqueous was extracted with EtOAc (2 x 20 mL). All the organics were combined, dried over anhydrous Na2S04, filtered. The solvent was removed by rotary evaporator to yield yellow residue, which was purified by column chromatography on silica gel (hexanes: ethyl acetate) to provide 247-139-002 (181 mg, 39%) as yellow solid. ¾ NMR (300 MHz, CDC13): 8.54 (s, 1H), 8.30 (s, 1H), 8.14 (s, 1H), 7.70-7.60 (m, 2H), 7.57 (dd, 1H), 7.40 (dd, 1H), 6.74 (s, 1H), 1.46 (s, 9H); R 0.40 (hexanes: EtOAc, 1 : 1) [UV].
39% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 2h; 6.46. tert-Butyl 6-cyano-2-(2-cyanoimidazo[1,2-a]pyridin-6-yl)-1H-indole-1-carboxylate (I-17) To a 50mL round bottom flask was added 1-(tert-butoxycarbonyl)-6-cyano-1H-indol-2-ylboronic acid (6) (417mg, 1.46 mmol), 6-bromoimidazo[1,2-a]pyridine-2-carbonitrile (11) (270 mg, 1.21 mmol), Pd(Ph3P)4 (140mg, 0.12 mmol), Na2CO3 (1M, 7.3 mL), toluene (24.0 mL) and EtOH (12.0 mL). The resultant brownmixture turned black upon heating to 80°C. The reaction mixture was stirred at this temperature for 2 hand cooled to room temperature. The organic layer was separated and the aqueous was extracted withEtOAc (2 x 20 mL). All the organics were combined, dried over anhydrous Na2SO4, filtered. The solventwas removed by rotary evaporator to yield yellow residue, which was purified by columnchromatography on silica gel (hexanes: ethyl acetate) to provide I-17 (181 mg, 39%) as yellow solid;
  • 11
  • [ 913835-67-3 ]
  • [ 1428230-59-4 ]
  • [ 1428230-60-7 ]
YieldReaction ConditionsOperation in experiment
41% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 1h; Inert atmosphere; 2,5-Bis(N-Boc-6-cyanoindol-2-yl)pyridine A solution of Ar-Boc-6-cyano-2-(5-bromopyridin-2-yl)indole (401 mg, 1.0 mmol), N-Boc-6- cyanoindole-2-boronic acid (301 mg, 1.0 mmol), and Pd(PPh3)4 (15 mg) in 10% EtOH/toluene (12 mL) was sparged with argon gas for 10 minutes, then a 2.0 M aqueous solution of sodium carbonate (1.0 mL, 2.0 mmol) was added. The reaction was heated to 100 °C in a sealed tube for 1 hour, then cooled to room temperature and diluted with EtOAc (50 mL) and brine (50 mL). The organic layer was separated, dried over MgS04, filtered, and evaporated to yield an orange oil which was subjected to flash chromatography on silica gel with 2: 1 hex:EtOAc. Product-containing fractions were pooled and evaporated to yield a yellow solid that was recrystallized from boiling CH2Cl2 hexane to yield228 mg (41 %) of product as a crystalline yellow solid: Rf 0.17 (3: 1 hex:EtOAc); ¾-NMR (300 MHz, CDC13): δ 8.76 (d, 1H), 8.56 (s, 1H), 8.51 (s, 1H), 7.86 (dd, 1H), 7.70-7.61 (m, 3H), 7.56-7.51 (m, 2H), 6.88 (s, 1H), 6.74 (s, lh), 1.48 (s, 9H), 1.45 (s, 9H).
41% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 1h; Inert atmosphere; Sealed tube; 2,5-Bis(N-Boc-6-cyanoindol-2-yl)pyridine A solution of Ar-Boc-6-cyano-2-(5-bromopyridin-2-yl)indole (401 mg, 1.0 mmol), N-Boc-6-cyanoindole-2-boronic acid (301 mg, 1.0 mmol), and Pd(PPh3)4 (15 mg) in 10% EtOH/toluene (12 mL) is sparged with argon gas for 10 minutes, then a 2.0 M aqueous solution of sodium carbonate (1.0 mL, 2.0 mmol) is added. The reaction is heated to 100 °C in a sealed tube for 1 hour, then cooled to room temperature and diluted with EtOAc (50 mL) and brine (50 mL). The organic layer is separated, dried over MgS04, filtered, and evaporated to yield an orangeoil which is subjected to flash chromatography on silica gel with 2: 1 hex:EtOAc. Product-containing fractions were pooled and evaporated to yield a yellow solid that was recrystallized from boiling CH2Cl2 hexane to yield 228 mg (41 ) of 2,5-Bis(ALBoc-6-cyanoindol-2-yl)pyridine as a crystalline yellow solid. 'H-NMR (300 MHz, CDC13): δ 8.76 (d, 1H), 8.56 (s, 1H), 8.51 (s, 1H), 7.86 (dd, 1H), 7.70-7.61 (m, 3H), 7.56-7.51 (m, 2H), 6.88 (s, 1H), 6.74 (s, lh), 1.48 (s, 9H), 1.45 (s, 9H); mp >300 °C; Rf 0.17 (3: 1 hex:EOAc)
38% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 7h; 5.2.31 2,5-Bis(N-Boc-6-cyanoindol-2-yl)pyridine (32) To solution of N-Boc-2-(5-bromopyridin-2-yl)indole-6-carbonitrile (31; 269mg, 0.68mmol) and N-Boc-6-cyanoindole-2-boronic acid (9; 387mg, 1.35mmol) dissolved in toluene (14mL) were added tetrakis(triphenylphosphine)palladium (0) (79mg, 0.07mmol) and aqueous sodium carbonate (1.0M, 4.0mL, 4.0mmol). The resulting mixture was heated to 80°C for 7h, then cooled to room temperature and poured into EtOAc (10mL) and water (5mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (2×10mL). The combined organic extracts were evaporated, and the residue was subjected to flash chromatography on silica gel with 0-75% EtOAc/hexane. Product-containing fractions were pooled and evaporated to provide 146mg (38%) of product as a pale yellow solid: Rf 0.23 (1:1 hexane/EtOAc); 1H NMR (CDCl3) δ 8.77 (s, 1H), 8.56 (s, 1H), 8.51 (s, 1H), 7.89 (dd, 1H), 7.70-7.62 (m, 3H), 7.56-7.51 (m, 2H), 6.88 (s, 1H), 6.74 (s, 1H), 1.48 (s, 9H), 1.43 (s, 9H).
  • 12
  • [ 913835-67-3 ]
  • [ 1428230-64-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 2 h / 70 °C / Inert atmosphere
  • 13
  • [ 913835-67-3 ]
  • [ 1429919-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,2-dimethoxyethane / 3.5 h / 78 °C / Inert atmosphere
  • 14
  • [ 913835-67-3 ]
  • [ 1428230-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,2-dimethoxyethane / 3.5 h / 78 °C / Inert atmosphere 3: tetraphosphorus decasulfide / 3 h / 120 °C
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,2-dimethoxyethane / 3.5 h / 78 °C / Inert atmosphere 3.1: tetraphosphorus decasulfide / 3 h / 120 °C / Sealed tube 3.2: Reverse phase C18 column chromatography
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