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Product Details of 4-(Boc-amino)benzeneboronic acid pinacol ester

CAS No. :330793-01-6
Formula : C17H26BNO4
M.W : 319.20
SMILES Code : CC(C)(C)OC(=O)NC1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1
MDL No. :MFCD02179439
InChI Key :HSJNIOYPTSKQBD-UHFFFAOYSA-N
Pubchem ID :2734617

Safety of 4-(Boc-amino)benzeneboronic acid pinacol ester

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-(Boc-amino)benzeneboronic acid pinacol ester

* 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 [ 330793-01-6 ]

[ 330793-01-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 73183-34-3 ]
  • [ 131818-17-2 ]
  • [ 330793-01-6 ]
YieldReaction ConditionsOperation in experiment
36% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; A mixture of bis(pinacolato)diboron (10.5 g, 41.5 mmol), 4 (7.75 g, 28.5 mmol), Pd(dppf)Cl2 (0.79 g, 1.1 mmol) and potassium acetate (7.0 g, 71.4 mmol) in dry dioxane (100 mL) was added into a 250 mL round bottom flask. The mixture was stirred for 12 h at 110 C under the protection of argon. After being cooled to room temperature, it was filtered and the filtrate was concentrated on a rotary evaporator. The residue was subjected to column chromatography over silica gel (PE/EA 10:1) to give 5 (3.26 g, 36%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 9.53(s, 1H), 7.56(d, J = 8.5 Hz, 2H), 7.47(d, J = 8.5 Hz, 2H), 1.48(s, 9H), 1.29(s, 12H).
With potassium acetate; In n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; b tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1'-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).
With potassium acetate; In n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; b) tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate A mixture of tert-butyl N-[(4-bromophenyl)carbamate (5.95 g, 0.0219 mol), diboron pinacol ester (6.67 g, 0.0263 mol), [1.1'-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (1:1) (0.536 g, 0.00066 mol) and potassium acetate (6.47 g, 0.066 mol) in N,N-dimethylformamide (120 mL) was heated at 80 C. under an atmosphere of nitrogen for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent removed under reduced pressure. Dichloromethane (100 mL) was added to the residue and the resulting solid was removed by filtration through a pad of Celite. The filtrate was concentrated to leave a yellow oil which was purified by flash chromatography on silica using ethyl acetate/n-heptane (7:93) as mobile phase. The resulting fractions were concentrated, the residue was triturated in n-heptane and the precipitate collected by filtration to yield tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (6.0 g, 0.0188 mol) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.50(s, 1H), 7.55 (d, 2H), 7.46 (d, 2H), 1.47 (s, 9H), 1.27 (s, 12H).
  • 2
  • [ 40000-20-2 ]
  • [ 330793-01-6 ]
  • [ 1334286-48-4 ]
  • 3
  • [ 78137-76-5 ]
  • [ 330793-01-6 ]
  • tert-butyl (4'-hydroxy-2'-nitro-[1,1'-biphenyl]-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 110℃; for 12h; General procedure: Palladium tetraphenylphosphine (115mg, 0.10mmol) and potassium carbonate solution (2M, 100muL) were added to a solution of 4-bromo-2-nitrophenol (150mg, 0.69mmol) and boronic ester (300mg, 0.82mmol) in dioxane (40mL) and the mixture was refluxed at 110°C for 12h. After 12h, the reaction mixture was concentrated to dryness and the residue so obtained was purified via column chromatography (SiO2, 100:1, CH2Cl2: acetone) to afford desired product as a yellow amorphous solid (136mg, 60percent).
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 110℃; for 12h;Reflux; tert-butyl (4'-hydroxy-2'-nitro-[1,1'-biphenyl]-4-yl)carbamate (32b): Palladium tetraphenylphosphine (0.10 mmol) and potassium carbonate solution (2M, 100 muL) were added to a solution of phenol (30b, 0.69 mmol) and boronic ester (0.82 mmol) in dioxane (10 mL) and the mixture was refluxed at 110 oC for 12 hours. After 12 hours, the reaction mixture was concentrated to dryness and the residue so obtained was purified via column chromatography (SiO2, 100:1, CH2Cl2:acetone) to afford desired product as a yellow amorphous solid (210 mg, 72percent). 1H NMR (500 MHz, chloroform-d) delta 7.40 (d, J = 8.3 Hz, 2H), 7.32 (d, J = 2.6 Hz, 1H), 7.28 (d, J = 5.0 Hz, 1H), 7.23? 7.17 (m, 2H), 7.07 (dd, J = 8.4, 2.6 Hz, 1H), 6.53 (s, 1H), 5.47 (s, 1H), 1.54 (s, 9H).13C NMR (126 MHz, CDCl3) delta 155.35, 153.00, 149.83, 138.39, 133.34, 132.05, 129.00, 128.64, 119.86, 118.99, 111.40, 81.16, 28.64. HRMS (ESI-) m/z [M-H+] calcd for C17H18N2O5 329.1137, found 329.1132
  • 4
  • [ 7597-22-0 ]
  • [ 330793-01-6 ]
  • [ 1197159-91-3 ]
  • 5
  • [ 25015-63-8 ]
  • [ 131818-17-2 ]
  • [ 330793-01-6 ]
 

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