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[ CAS No. 918331-73-4 ]

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Chemical Structure| 918331-73-4
Chemical Structure| 918331-73-4
Structure of 918331-73-4 * Storage: {[proInfo.prStorage]}

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Product Details of [ 918331-73-4 ]

CAS No. :918331-73-4 MDL No. :MFCD18837624
Formula : C13H16BClO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :282.53 g/mol Pubchem ID :-
Synonyms :

Safety of [ 918331-73-4 ]

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

Application In Synthesis of [ 918331-73-4 ]

  • Downstream synthetic route of [ 918331-73-4 ]

[ 918331-73-4 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 918331-73-4 ]
  • [ 765-30-0 ]
  • [ 1057393-55-1 ]
YieldReaction ConditionsOperation in experiment
72% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 24h; 10 To a solution of Intermediate 9 (294 mg, 1.04 mmol) in dimethylformamide (3 mL) was added cyclopropylamine (88 μL, 1.28 mmol), diisopropylethylamine (408 μL, 2.34 mmol) and O-(7-azabenzotriazol-1-yl)-λ/,λ/,λ/' λ/'-tetramethyluronium hexafluorophosphate (388 mg, 1.02 mmol). The clear solution was stirred at room temperature for 1 day. Subsequently, the dimethylformamide was evaporated and the residue treated with ethyl acetate (75 mL). This organic phase was washed with aqueous sodium bicarbonate (4%) (100 mL), water and brine, dried and concentrated to afford an oily residue. This oil was treated with a mixture of hexanes-diethyl ether yielding 240 mg (72%) of the title compound.LRMS (m/z): 240 (M+1)+ (corresponding to the boronic acid generated within the HPLC column). 1H-NMR δ (DMSO-d6): 0.58 (m, 2H), 0.70 (m, 2H), 1.33 (s, 12H), 2.84 (m, 1 H),7.51 (d, J=8.3 Hz, 1 H), 7.88 (d, J=8.3 Hz, 1 H), 8.06 (s, 1 H), 8.59 (brs 1 H).
  • 3
  • [ 42860-10-6 ]
  • [ 73183-34-3 ]
  • [ 918331-73-4 ]
YieldReaction ConditionsOperation in experiment
54% In a Schlenk tube were charged <strong>[42860-10-6]3-bromo-4-chlorobenzoic acid</strong> (2.00 g, 8.49 mmol), bis(pinacolato)diboron (3.23 g, 12.72 mmol), potassium acetate (4.17 g, 42.49 mmol) and N,N'-dimethylformamide (40 mL). The mixture was submitted to three vacuum-argon cycles, then [1,1'-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) complex with dichloromethane (1:1) (700 mg, 0.87 mmol) was added and the reaction vessel was purged in the same way and then stirred at 80 °C under argon for 5 hours. Subsequently, the solvent was removed in vacuo, 2M aqueous sodium hydroxide solution (50 mL) was added and the mixture was extracted with ethyl acetate. The mixture was cooled in an ice-water bath and the aqueous phase was acidified with 5M aqueous hydrochloric acid to pH 3. The solid that formed was filtered, washed with water and dried to give the title compound (1.30 g, 54percent) as a white solid. LRMS (m/z): 199 (M-1)- (corresponding to the boronic acid generated under the HPLC conditions). 1H-NMR delta (DMSO-d6): 1.34 (s, 12H), 7.58 (d, J=8.3 Hz, 1H), 8.00 (d, J=8.3 Hz, 1H), 8.24 (s, 1H), 12.28 (brs, 1 H).
54% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 80℃; for 5h; In a Schlenk tube were charged <strong>[42860-10-6]3-bromo-4-chlorobenzoic acid</strong> (2 g, 8.49 mmol), 4,4,5,5,4I,4I,5',5'-Octamethyl-[2,2l]bi[[1 ,3,2]dioxaborolanyl] (3.23 g, 12.72 mmol), potassium acetate (4.17 g, 42.49 mmol) and dimethylformamide (40 mL). The mixture was submitted to three vacuum argon cycles, then [1 ,1'-bis(diphenylphosphino)ferrocene]dichloro- palladium(ll) complex with dichloromethane (1 :1) (700 mg, 0.87 mmol) was added and the mixture purged in the same way. The reaction was stirred at 8O0C under argon for 5 hours. <n="40"/>Subsequently, the dimethylformamide was removed under vacuum, sodium hydroxide 2N (50 mL) was added and this mixture extracted with ethyl acetate (2x100 ml_). The aqueous phase was acidified with hydrochloric acid 5N until pH=3 in an ice-water bath, appearing a solid that was filtered affording 1.3 g (54percent) of the title compound.LRMS (m/z): 199 (M-I)+ (corresponding to the boronic acid generated within theHPLC column).1H-NMR delta (DMSO-d6): 1.34 (s, 12H), 7.58 (d, J=8.3 Hz, 1 H), 8.00 (d, J=8.3 Hz,1 H), 8.24 (s, 1 H), 12.28 (brs, 1 H).
  • 4
  • [ 918331-73-4 ]
  • [ 1210812-83-1 ]
  • [ 1214882-15-1 ]
YieldReaction ConditionsOperation in experiment
10% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate monohydrate In 1,4-dioxane; water at 55 - 105℃;
  • 5
  • [ 918331-73-4 ]
  • [ 591-18-4 ]
  • 3′-bromo-6-chloro-[1,1′-biphenyl]-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.6% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; caesium carbonate In dimethyl sulfoxide at 90℃;
  • 6
  • [ 918331-73-4 ]
  • 6-chloro-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 90 °C 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 90 °C
  • 7
  • [ 918331-73-4 ]
  • tert-butyl ((1′-(6-chloro-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-carbonyl)-2H-spiro[benzofuran-3,4′-piperidin]-5-yl)methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate; potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 90 °C 2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 90 °C 3.1: dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 0.25 h / 0 °C 3.2: 12 h / 20 °C
  • 8
  • [ 918331-73-4 ]
  • (5′-(5-(aminomethyl)-2H-spiro[benzofuran-3,4′-piperidine]-1′-carbonyl)-2′-chloro-[1,1′-biphenyl]-3-yl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate; potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 90 °C 2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 90 °C 3.1: dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 0.25 h / 0 °C 3.2: 12 h / 20 °C 4.1: hydrogenchloride / 1,4-dioxane / 20 °C
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