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[ CAS No. 116378-40-6 ]

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Chemical Structure| 116378-40-6
Chemical Structure| 116378-40-6
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Product Details of [ 116378-40-6 ]

CAS No. :116378-40-6 MDL No. :MFCD02179466
Formula : C7H8BNO4 Boiling Point : 545.498°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :180.95 g/mol Pubchem ID :-
Synonyms :

Safety of [ 116378-40-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 116378-40-6 ]

  • Downstream synthetic route of [ 116378-40-6 ]

[ 116378-40-6 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 463-71-8 ]
  • [ 116378-40-6 ]
  • 3-Isothiocyanato-5-carboxyphenylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With hydrogenchloride at 20℃; for 0.333333h;
  • 2
  • [ 101084-81-5 ]
  • [ 116378-40-6 ]
YieldReaction ConditionsOperation in experiment
97.1% With palladium 10% on activated carbon; hydrogen; In methanol; for 6h; The 7.5g between carboxyl phenylo boric acid (45.2mmol) by adding 25 ml of concentrated sulfuric acid, under rapid stirring state by adding 25 ml fuming nitric acid, ice water bath cooling. Stirring the reaction 15 min evacuation de-ice water bath, to continue reaction 15 min. In ice water into the reaction liquid, precipitate, filtering, washing 5 times, re-crystallization with water, to obtain white solid 3-nitro-5-carboxyl phenylo boric acid 6.01g, yield 63.0% ; the 1.50g3-carboxy-5-nitro-phenylboronic acid (7.1mmol), 20 ml methanol, 10% Pd/C0 . 2g by adding 50 ml in three-necked bottle, catalytic hydrogenolysis 6h. Filtered to remove palladium-carbon, the filtrate is evaporated to dryness, to obtain white powder solid 3-amino-5-carboxyl phenylo boric acid 1.25g, yield 97.1%.
71% With hydrogen;nickel; In ethanol; for 6h; To make desired compound, a solution of <strong>[101084-81-5]3-carboxyl-5-nitrophenylboronic acid</strong> (422 mg, 2 mmol) in absolute ethanol (5 ml) was hydrogenated in the presence of Raney Nickel (150 mg) for 6 hours. The catalyst was removed by filtration and the solvent was evaporated to dryness, then the residue was recrystallized from water to give 257 mg (71% yield) of the desired compound as a pale yellow powder
With hydrogen;palladium on activated charcoal; In methanol; under 2068.65 Torr; for 1.5h; 3-CARBOXY-5-NITROPHENYLBORONIC acid (250 mg, 1.1 mmol) was added to a suspension of palladium on charcoal (12 mg) in methanol (15 ml) and reduced in an atmosphere of hydrogen (40 psi). After 1.5 hours, the reaction mixture was filtered over celite and the filtrate concentrated under reduced pressure. The crude (200 mg, about 1.1 mmol) was then dissolved in water (2 ml) and dioxane (1 ml). A 10 N aqueous solution of sodium hydroxide (0.33 ml, 3 eq. ) was added. To the mixture a solution of methanesulfonyl chloride (0.1 ml, 1.2 mmol, 1. 1 eq. ) in dichloromethane (1 ml) at 0C was added dropwise. The reaction mixture was then stirred at room temperature for 2 hours and acidified with a 5% citric acid aqueous solution. The product was extracted with ethyl acetate (2 x 10 ml). The combined organic layers were dried (NA2S04) and concentrated under reduced pressure. The crude (130 mg, 0.5 mmol) was then coupled with intermediate 1 (178 mg, 0.5 mmol) under the Suzuki conditions operating as described for compound 1. The product was extracted with ethyl acetate (2 X 15 ml), dried (NA2SO4) and concentrated under reduced pressure. The product was purified on a Varian Mega Bond ChemElut (SI02) eluting with CH2CLZ/METHANOL/ACETIC acid (99: 1: 0.05 V/V/V) to give compound 6 as a pale yellow solid (13 mg, 0.02 mmol, 5% yield). MS: 534 [M+H] + HPLC/MS: Gilson instrument equipped with a C18 column Zorbax SBC18 (3.5 JIM, 2.1 x 50 MM) coupled with a diode array UV detector (220 NM) and a Finnigan Aqa mass SPECTROMETER (electron spray, positive ionization). The following settings were used: flow rate: 1 ML/MIN ; column temperature: 40C ; gradient elution A/B (eluent A: 0.5% formic acid in water; eluent B: 0.5% formic acid in ACETONITRILE) ; t = 0 min. , A/B = 95: 5, t = 8 min. , A/B =5 : 95; Rt 4. 36 min.
aluminum nickel; In ethanol; EXAMPLE 2D 3-Amino-5-carboxyphenylboronic Acid A solution of <strong>[101084-81-5]3-nitro-5-carboxyphenylboronic acid</strong> (3.3 g, 0.016 mol) in absolute ethanol (25 ml) was hydrogenated in the presence of Raney Nickel (1 g) at 50 lbs per square inch for 4 hours in a Parr shaker. The catalyst was removed by filtration and the solvent was removed on a rotary evaporator. The solid obtained was recrystallized from water. M.P. 210-12 C.

YieldReaction ConditionsOperation in experiment
/BRN= 3278887/;
  • 4
  • [ 116378-40-6 ]
  • [ 5416-93-3 ]
  • [ 75-31-0 ]
  • 5-(iso-propylaminocarbonyl)-N-(4'-methoxyphenylaminocarbonyl)-3-aminophenylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Multistep reaction.;
  • 5
  • [ 931-53-3 ]
  • [ 116378-40-6 ]
  • [ 64-19-7 ]
  • [ 75-31-0 ]
  • [ 78-84-2 ]
  • N-(acetyl)-N-(1'-cyclohexylaminocarbonyl-2'-methylpropane)-3-amino-5-(isopropylaminocarbonyl)phenylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Multistep reaction.;
  • 6
  • [ 116378-40-6 ]
  • [ 810671-79-5 ]
  • 3-amino-5-[(4-ethylcarbamoyl-phenyl)-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-methyl]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1-methyl-pyrrolidin-2-one at 180℃; for 0.166667h; microwave irradiation;
  • 7
  • [ 116378-40-6 ]
  • [ 351002-11-4 ]
  • 3-amino-5-(2-morpholin-4-yl-4-oxo-4<i>H</i>-chromen-8-yl)-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 90℃; for 18h;
  • 8
  • [ 116378-40-6 ]
  • [ 503467-98-9 ]
  • 3-amino-5-(2-morpholin-4-yl-4-oxo-4H-chromen-7-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 90℃; for 18h;
  • 9
  • [ 116378-40-6 ]
  • [ 130735-60-3 ]
  • 3-amino-5-(2-morpholin-4-yl-4-oxo-4<i>H</i>-chromen-6-yl)-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 90℃; for 18h;
  • 11
  • [ 2689-65-8 ]
  • [ 116378-40-6 ]
  • 3-amino-5-(5-formyl-furan-2-yl)-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In ethanol; toluene at 90℃; for 19h;
  • 12
  • [ 25487-66-5 ]
  • [ 116378-40-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 53 percent / conc. H2SO4; fuming HNO3 / 0.75 h / 20 °C 2: 92 percent / H2 / Raney Ni / ethanol / 4 h / 2585.74 Torr
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 0.5 h / Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol / 6 h
  • 13
  • [ 116378-40-6 ]
  • [ 124-63-0 ]
  • C8H10BNO6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (3-amino-5-carboxylphenyl)boronic acid; methanesulfonyl chloride With sodium hydroxide In 1,4-dioxane; dichloromethane; water at 0 - 20℃; for 2h; Stage #2: With citric acid In 1,4-dioxane; dichloromethane; water 8 3-CARBOXY-5-NITROPHENYLBORONIC acid (250 mg, 1.1 mmol) was added to a suspension of palladium on charcoal (12 mg) in methanol (15 ml) and reduced in an atmosphere of hydrogen (40 psi). After 1.5 hours, the reaction mixture was filtered over celite and the filtrate concentrated under reduced pressure. The crude (200 mg, about 1.1 mmol) was then dissolved in water (2 ml) and dioxane (1 ml). A 10 N aqueous solution of sodium hydroxide (0.33 ml, 3 eq. ) was added. To the mixture a solution of methanesulfonyl chloride (0.1 ml, 1.2 mmol, 1. 1 eq. ) in dichloromethane (1 ml) at 0°C was added dropwise. The reaction mixture was then stirred at room temperature for 2 hours and acidified with a 5% citric acid aqueous solution. The product was extracted with ethyl acetate (2 x 10 ml). The combined organic layers were dried (NA2S04) and concentrated under reduced pressure. The crude (130 mg, 0.5 mmol) was then coupled with intermediate 1 (178 mg, 0.5 mmol) under the Suzuki conditions operating as described for compound 1. The product was extracted with ethyl acetate (2 X 15 ml), dried (NA2SO4) and concentrated under reduced pressure. The product was purified on a Varian Mega Bond ChemElut (SI02) eluting with CH2CLZ/METHANOL/ACETIC acid (99: 1: 0.05 V/V/V) to give compound 6 as a pale yellow solid (13 mg, 0.02 mmol, 5% yield). MS: 534 [M+H] + HPLC/MS: Gilson instrument equipped with a C18 column Zorbax SBC18 (3.5 JIM, 2.1 x 50 MM) coupled with a diode array UV detector (220 NM) and a Finnigan Aqa mass SPECTROMETER (electron spray, positive ionization). The following settings were used: flow rate: 1 ML/MIN ; column temperature: 40°C ; gradient elution A/B (eluent A: 0.5% formic acid in water; eluent B: 0.5% formic acid in ACETONITRILE) ; t = 0 min. , A/B = 95: 5, t = 8 min. , A/B =5 : 95; Rt 4. 36 min.
  • 14
  • [ 116378-40-6 ]
  • [ 874347-49-6 ]
  • [ 943238-76-4 ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: (3-amino-5-carboxylphenyl)boronic acid; 3-iodo-2-methoxy-benzaldehyde With potassium carbonate In dichloromethane; water at 60℃; for 6h; Stage #2: With hydrogenchloride In dichloromethane; water 2.A Part A; Under argon atmosphere, aryl bromide 3 (2.32 mmol), boronic acid 14 (2.8 mmol), phosphine ligand (0.1 mmol), palladium acetate (0.5 mmol), and potassium carbonate (9.3 mmol) were suspended in degassed water and heated with stirring at 60° C. for 8 h (K. W. Anderson and S. L. Buchwald, Ang. Chem. Int. Ed., 2005, 44, 2). The mixture was poured into DCM (40 mL) and water (20 mL), and the pH of the aqueous layer was adjusted to 3 with 2N HCl. The layers were mixed and separated, and the aqueous layer was extracted with DCM (20 mL). The organic layers were combined, washed with saturated aqueous NaCl, dried over sodium sulfate, and concentrated to a light yellow oil. Purification by silica gel chromatography (0.5% HOAc/20-40% ethyl acetate/hexanes) yielded pale yellow solid (33% yield).
  • 15
  • [ 958646-54-3 ]
  • [ 116378-40-6 ]
  • C15H15NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In tetrahydrofuran; water at 65℃; for 2h; 10.B Part B; To a degassed solution of iodide 29 (1.0 g, 3.8 mmol, 1.0 eq) and boronic acid 5 (1.37 g, 7.6 mmol, 2.0 eq) in a THF/water mixture (1:5, 18 mL) was added palladium acetate (22 mg, 0.09 mmol, 0.025 eq), potassium carbonate (2.1 g, 15 mmol, 4 eq) and finally a sulfated S-Phos ligand (100 mg, 0.19 mmol, 0.050 eq) (Anderson, K. W.; et. al., Angew. Chemie 2005, 44, 2922). Under an argon atmosphere, the clear mixture was heated at 65° C. for 2 h with vigorous stirring. The reaction mixture was allowed to cool to rt and was then diluted with THF (3 mL) and acetic acid (3 mL). To this stirring mixture was added formalin solution (2.4 mL, 30 mmol, 8.0 eq) and sodium cyanoborohydride (710.0 mg, 11 mmol, 3.0 eq). After stirring for 15 min, the mixture was diluted with water (50 mL) and extracted twice with EtOAc (2×75 mL). The combined organic layers were washed with saturated aqueous sodium chloride (30 mL) and dried over sodium sulfate. Concentration in vacuo provided a pale yellow oil of 30 that was used in the subsequent reaction without further purification.
  • 16
  • C24H35IN2O5 [ No CAS ]
  • [ 116378-40-6 ]
  • C31H41N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In tetrahydrofuran; water at 65℃; for 4h; 1.I Part I; To a degassed (Ar) solution of pyrrolidine 12 (190 mg, 0.34 mmol) in a THF/H2O mixture (1:1, 4 mL) was added boronic acid 13 (120 mg, 0.68 mmol), palladium acetate (12 mg, 0.05 mmol), potassium carbonate (190 mg, 1.4 mmol) and finally phosphine ligand (Anderson, K. W.; et. al., Angew. Chemie 2005, 44, 2922) (54 mg, 0.1 mmol). The reaction was heated to 65° C. After 4 h at 65° C., the reaction mixture was allowed to cool to 23° C. over the course of an hour, diluted with DCM and filtered through a pad of sand and celite. The filtrate was. then extracted using DCM (50 mL) from a pH 4 water solution (20 mL). The aqueous layer was separated and extracted with DCM (2×20 mL), the combined organic extracts were washed with brine (15 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude residue was used in the subsequent reaction without further purification.
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