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Chemical Structure| 1032528-06-5
Chemical Structure| 1032528-06-5
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CAS No. :1032528-06-5 MDL No. :MFCD18762017
Formula : C21H32BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :AYUCJBOQVMWQJD-UHFFFAOYSA-N
M.W : 373.29 Pubchem ID :58326444
Synonyms :

Safety of [ 1032528-06-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1032528-06-5 ]

* 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.

  • Upstream synthesis route of [ 1032528-06-5 ]
  • Downstream synthetic route of [ 1032528-06-5 ]

[ 1032528-06-5 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
91.3% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran for 5 h; Reflux Step 5: tert-Butyl {1 -[4-(4,4,5,5-tetramethy-1 ,3,2-dioxaborolan-2-yl)phenyl]- cyclobutyl}carbamate [lnt-1 B] 27.75 g (55 mmol) [1-(4-Bromophenyl)cyclobutyl]carbamic acid fe/f-butyl ester, 23.76 mmol (93.6 mmol) bis-(pinacolato)diboron, 25 g (255 mmol) potassium acetate and 2.08 g (2.55 mmol) 1 , 1 '-bis(diphenylphosphino)ferrocenedichloro- palladium(ll) in 500 mL degassed THF were heated for three hours at reflux. The colour of the reaction mixture turned from dark red to black. Due to an incomplete reaction heating was continued for another two hours. The reaction mixture was poured on water (400 mL) and diluted with ethyl acetate (700 mL). After stirring for 30' the organic phase was separated and the aqueous phase was reextracted twice with ethyl acetate (400 and 200 mL). The combined organic extracts were washed with brine (200 mL) and dried (sodium sulfate). After evaporation of the solvent the residue was purified by chromatography (Biotage) yielding 28.99 g (91.3percent) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 7.51 -7.67 (m, 3H), 7.38 (d, 2H), 2.22-2 42 (m, 4H), 1.88-2.02 (m, 1 H), 1.63-1.80 (m, 1 H), 1.00-1.38 (m, 21 H) ppm.
90.8% With potassium acetate In tetrahydrofuranReflux 10 g (30.7 mmol) [1 -(4-Bromophenyl)-cyclobutyl]-carbamic acid tert. -butyl ester, 8.56 g (33.7 mmol) bis-(pinacolato)diboron, 750.9 mg (0.92 mmol) 1 ,1 '- bis(diphenylphosphino)ferrocenedichloropalladium(ll) and 9.03 g (92 mmol) potassium acetate are given in 180 mL THF which has been degassed for 10'. The reaction mixture is heated at reflux until the starting material has disappeared (usually two hours). At 60 °C the reaction mixture turns dark. The reaction mixture is poured on water (200 ml_) and ethyl acetate (500 ml_) is added. The mixture is vigorously stirred for two hours. After separation of the organic phase the aqueous phase is extracted once more with ethyl acetate (300 ml_). The combined organic extracts are washed with brine and dried (sodium sulfate). After evaporation of the solvent the residue, a black oil, is purified by chromatography on silicagel (eluents: hexane/ ethyl acetate). 10.4 g (90.8percent) of the title compound are obtained.MS (ES+, M+1 ): 3741H-NMR (400 MHz, d6-DMSO): δ 7.61 (d, 2H), 7.55-7.65 (br. 1 H), 7.35 (d, 2H), 2.22-2.42 (m, 4H), 1 .88-2.02 (m, 1 H), 1 .65-1 .82 (m, 1 H), 1 .00-1 .38 (m, 21 H).
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 10 h; Inert atmosphere Potassium acetate (2.41 g) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (6.25 g) are sequentially added to a DMF (25 mL) solution of the product (3.21 g) of Reference Example 56(3), and the mixture was placed in a nitrogen atmosphere. [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (360 mg) was added thereto, and the mixture was stirred at 80° C. for 10 hours.
The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate.
The combined organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate) to give the desired product (3.20 g, yield: 87percent) as a colorless solid.
1H-NMR (CDCl3) δ: 7.79 (2H, d, J=8.0 Hz), 7.43 (2H, d, J=8.0 Hz), 5.07 (1H, br s), 2.59-2.31 (4H, m), 2.14-2.03 (1H, m), 1.90-1.78 (1H, m), 1.36 (9H, s), 1.34 (12H, s)
ESI-MS m/z 374 (MH+)
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In water; N,N-dimethyl-formamide at 80℃; for 10 h; Inert atmosphere Reference Example 56(4) tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutylcarbamate
Potassium acetate (2.41 g) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (6.25 g) are sequentially added to a DMF (25 mL) solution of the product (3.21 g) of Reference Example 56(3), and the mixture was placed in a nitrogen atmosphere. [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (360 mg) was added thereto, and the mixture was stirred at 80°C for 10 hours.
The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate.
The combined organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate) to give the desired product (3.20 g, yield: 87percent) as a colorless solid.
1H-NMR (CDCl3) δ: 7.79 (2H, d, J = 8.0 Hz), 7.43 (2H, d, J = 8.0 Hz), 5.07 (1H, br s), 2.59 - 2.31 (4H, m), 2.14 - 2.03 (1H, m), 1.90 - 1.78 (1H, m), 1.36 (9H, s), 1.34 (23H, s)
ESI-MS m/z374 (MH+)

Reference: [1] Patent: WO2013/104611, 2013, A1, . Location in patent: Page/Page column 48
[2] Patent: WO2012/7416, 2012, A1, . Location in patent: Page/Page column 75; 76
[3] Patent: US2014/5185, 2014, A1, . Location in patent: Paragraph 0256-0258
[4] Patent: EP2868660, 2015, A1, . Location in patent: Paragraph 0172
[5] Patent: WO2012/7345, 2012, A2, . Location in patent: Page/Page column 243
[6] Patent: WO2016/102672, 2016, A2, . Location in patent: Page/Page column 111
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Reference: [1] Patent: US2008/161317, 2008, A1, . Location in patent: Page/Page column 71-72
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Reference: [1] Patent: WO2012/7345, 2012, A2,
[2] Patent: WO2013/104611, 2013, A1,
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Reference: [1] Patent: WO2012/7345, 2012, A2,
[2] Patent: WO2012/7416, 2012, A1,
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Reference: [1] Patent: WO2012/7416, 2012, A1,
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Reference: [1] Patent: US2014/5185, 2014, A1,
[2] Patent: EP2868660, 2015, A1,
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Reference: [1] Patent: US2014/5185, 2014, A1,
[2] Patent: EP2868660, 2015, A1,
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