912369-50-7|1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine| Ambeed

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Quality Control of [ 912369-50-7 ] Purity: 95% SDS Specification

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Product Details of [ 912369-50-7 ]

CAS No. :	912369-50-7
Formula :	C₁₆H₂₅BN₂O₂
M.W :	288.19
SMILES Code :	CC1(C)C(C)(C)OB(C2=CC=C(N3CCNCC3)C=C2)O1
MDL No. :	MFCD06795649
InChI Key :	KARUXRFAVXKQFZ-UHFFFAOYSA-N
Pubchem ID :	17750277

Safety of [ 912369-50-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 912369-50-7 ]

* 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 [ 912369-50-7 ]

[ 912369-50-7 ] Synthesis Path-Downstream 1~35

1
[ 470478-90-1 ]
[ 912369-50-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;	Step D: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine Into a 100 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (1.6 g, 4.12 mmol, 1.00 equiv) in dichloromethane (40 mL), followed by the addition of TMSOTf (1.5 g, 6.75 mmol, 1.60 equiv) dropwise with stirring at 0 C. To the above solution was added 6-dimethylpyridine (132.5 mg, 1.00 mmol, 0.30 equiv). The resulting solution was stirred for 3 hours at room temperature. The reaction was then quenched by the addition of 50 mL of saturated sodium bicarbonate aqueous. The resulting solution was extracted with ethyl acetate (30 mL*3). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10:1). This resulted in 854.0 mg (72%) of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine as off-white solid. LCMS (ES+): m/z 289.15 [M+H]+.
72%	With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;	Into a 100 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl]piperazine-1-carboxylate (1.6 g, 4.12 mmol, 1.00 equiv) in dichloromethane (40 mL), followed by the addition of TMSOTf (1.5 g, 6.75 mmol, 1.60 equiv) dropwise with stirring at 0 C. To the above solution was added 6-dimethylpyridine (132.5 mg, 1.00 mmol, 0.30 equiv). The resulting solution was stirred for 3 hours at room temperature. The reaction was then quenched by the addition of 50 mL of saturated sodium bicarbonate aqueous. The resulting solution was extracted with ethyl acetate (30 mL x 3). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10:1). This resulted in 854.0 mg (72%) of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine as off- white solid. LCMS (ES+): m/z 289.15 [M+H]+.
	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 2h;	Example 184; 2- {4- [4-(methylsulfonyl)piperazin-l-yl] phenyl}-4- [(3S)-piperidin-3~ylamino] thieno [3,2- c] py ridine-7-carboxamide; l-[4-(4,4,5,5-tetramethyl-l,3<2-dioxaborolan-2-yl)phenyllpiperazine; To tert-butyl 4- [4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]piperazine-l-carboxylate (235 mg, 0.656 mmol) is added 5.0 mL of 4N HCl in dioxane and the resulting solution is stirred at rt for two hours whereupon the solution is concentrated under reduced pressure to afford the title compound as a white solid. 1H NMR δ 9.14 (br s, IH), 7.54 (d, 2H), 6.96 (d, 2H), 3.43 (m, 4H), 3.18 (m, 4H), 1.25 (s, 12H).

References: [1]Patent: US2018/179183,2018,A1 .Location in patent: Paragraph 1400.
[2]Patent: WO2020/51564,2020,A1 .Location in patent: Paragraph 0672; 0673.
[3]Patent: WO2006/106326,2006,A1 .Location in patent: Page/Page column 133.

2
[ 912369-50-7 ]
[ 1297599-77-9 ]
[ 1297599-78-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 85℃; for 5h;	Solid Pd(dppf)Cl2 (dichloro[1,1'-ferrocenylbis(diphenyl-phosphine)]palladium(II), 47 mg, 0.06 mmol) was added to a dioxane/water solution (4 mL/1 mL) of 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine (213 mg, 0.75 mmol), trifluoro-methanesulfonic acid 2-amino-4-(4-fluoro-phenyl)-5-oxo-5H-indeno[1,2-d]pyrimidin-9-yl ester (250 mg, 0.57 mmol), and K2CO3(158 mg, 1.14 mmol) and the mixture was heated to 85 C. After 5 hours the mixture was cooled, diluted with water and the resulting precipitate was filtered. The collected solid was dissolved in THF and MeOH then dry packed onto silica gel. Column chromatography gave the title compound.

References: [1]Patent: US2011/105492,2011,A1 .Location in patent: Page/Page column 12.

3
[ 705263-10-1 ]
[ 912369-50-7 ]
[ 1435614-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.5h;Inert atmosphere; Microwave irradiation;	General procedure: In a μwave vial, 6-bromopyrazolo[1,5-a]pyrimidine, 9, (0.25 g, 1.26 mmol, 1.0 eq), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine, 10, (0.36 g, 1.26 mmol, 1.0 eq), and Pd(dppf)Cl2•DCM (52.0 mg, 0.06 mmol, 0.05 eq) were added. The μwave vial was evacuated under reduced pressure and purged with Argon (3x). To the mixture was added 1,4-dioxane (9 mL), followed by a solution of K3PO4 (0.54 g, 2.52 mmol, 2.0 eq) in H2O (4.0 mL). The reaction was heated to 150 C for 30 min under microwave irradiation. The reaction was added to EtOAc: H2O (1:1, 100 mL). The organic layer was separated, washed with H2O (25 mL), Brine (25 mL), dried (MgSO4), filtered and concentrated. The material was purified by reverse-phase HPLC (5-35% acetonitrile: H2O w/ 0.1% TFA) to afford 4-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine, 11 (0.25 g, 71% yield).

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3248 - 3252.

4
[ 912369-50-7 ]
[ 1175675-65-6 ]
9-benzenesulfonyl-4-chloro-6-(4-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)phenyl)-9H-pyrido[2,3-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 15h;	In a Schlenk tube, at r.t. and under inert atmosphere, Pd(Ph3)4 (0.1 eq), K2CO3 (3 eq) and boronic acid (1.3 eq) were added to a 0.04M suspension of 9-benzenesulfonyl-6-bromo-4-chloro-9H-pyrido[2,3-b]indole in THF/H2O 4:1 mixture. This solution was stirred at 70C for 15h. After cooling to r.t. and diluting with EtOAc, the mixture was filtered through a Celite pad. The solvents were removed under reduced pressure. The crude product was triturated in MeOH and filtered. Then, the remaining solid was purified by silica gel flash chromatography (DCM/MeOH 90:10) to afford the desired compound in 38% yield as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.57 (d, J = 1.8 Hz, 1H), 8.54 (d, J = 8.9 Hz, 1H), 8.43 (d, J = 5.4 Hz, 1H), 8.19 - 8.12 (m, 2H), 7.81 (dd, J = 8.8, 1.9 Hz, 1H), 7.59 (d, J = 8.7 Hz, 2H), 7.53 (t, J = 7.4 Hz, 1H), 7.42 (t, J = 7.6 Hz, 2H), 7.28 (d, J = 5.4 Hz, 1H), 7.03 (d, J = 8.8 Hz, 2H), 3.23 (dd, J = 6.2, 3.7 Hz, 4H), 3.08 (dd, J = 6.1, 3.7 Hz, 4H), 2.25 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 151.9 (C), 151.3 (C), 146.8 (CH), 138.6 (C), 138.5 (C), 137.4 (C), 136.5 (C), 134.2 (CH), 131.7 (C), 129.1 (CH), 128.0 (CH), 127.8 (CH), 127.7 (CH), 122.4 (C), 120.9 (CH), 120.4 (CH), 116.8 (C), 116.4 (CH), 115.0 (CH), 50.1 (CH2), 46.1 (CH2); MS (ESI) m/z: 503.1 [M+H]+.

References: [1]Patent: EP2662372,2013,A1 .Location in patent: Paragraph 0059.

5
[ 912369-50-7 ]
[ 86864-60-0 ]
[ 1560796-11-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With caesium carbonate; In acetonitrile; at 40℃;	A mixture of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (0.1 g, 0.5 mmol, from Boron Molecular), (2-bromoethoxy)(tert-butyl)dimethylsilane (0.18 g, 0.75 mmol) and cesium carbonate (0.32 g, 1.0 mmol) in acetonitrile (2.0 mL) was stirred at 40C. overnight. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford the desired product (0.2 g, 88%). LCMS calculated for C24H44BN2O3Si (M+H)+: m/z=447.3. Found 447.3.

References: [1]Patent: US2014/45814,2014,A1 .Location in patent: Paragraph 0354; 0355.

6
[ 912369-50-7 ]
2-(4-(4-(2-(3,5-dimethoxyphenylethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl)piperazin-1-yl)ethanol trifluoroacetic acid [ No CAS ]

References: [1]Patent: US2014/45814,2014,A1 .

7
[ 912369-50-7 ]
[ 79-03-8 ]
[ 1415794-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In tetrahydrofuran; at 20℃;	General procedure: To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) piperazine hydrochloride (419 mg, 1.29 mmol) and cesiumcarbonate (1.27 g, 3.9 mmol) in THF (30 mL) was added acetyl chloride (0.5 mL, 6.5 mmol). Then the mixture was stirred at room temperature overnight, extracted with EA, washed with NaHCO3 solution and brine. The organic solution was concentrated and purified by flash column chromatography, eluting with PE/EA, to give product as a white solid. The title compound was prepared according to the procedures of Intermediate 54 using <strong>[912369-50-7]1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine</strong>. MS (m/z): 345 (M+H)+.

References: [1]Patent: US2014/121200,2014,A1 .Location in patent: Paragraph 0286; 0287; 0288.

8
[ 67455-41-8 ]
[ 73183-34-3 ]
[ 912369-50-7 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv) followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg of NaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0-5 C followed by B2pin2 (2, 381 mg, 1.5 mmol, 3.0equiv) in MeOH (1.0 mL). This mixture was stirred 60 min.H2O (10 mL) was added to the reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layers were washed with sat. NaHCO3, dried over Na2SO4, followed by evaporation, and the crude residue was purified by flash chromatography.

References: [1]Synlett,2014,vol. 25,p. 1577 - 1584.

9
[ 912369-50-7 ]
5-(2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile [ No CAS ]
5-(1-(phenylsulfonyl)-2-(4-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 100℃; for 1h;	To stirring solution of 5-(2-iodo-1-(phenylsulfonyl)-1 H-pyrrolo[2,3- b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile (500 mg, 0.85 mmol), 1-(4- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)piperazine (270.7 mg, 0.94 mmol), and PdCI2(Ph3P)2 (60 mg, 0.085 mmol) in DMF (12 mL) were added solution of NaHC03 (215 mg, 2.56 mmol) in water (6 mL). The reaction was stirred at 100C for 1 h. The reaction mixture was diluted with dichloromethane, filtered through pad of silica gel washed with 10% MeOH/DCM and the solvent concentrated to dryness. The residue was purified by flash column chromatography on silica gel to afford 5-(1- (phenylsulfonyl)-2-(4-(piperazin-1-yl)phenyl)-1 H-pyrrolo[2,3-b]pyridin-4-yl)-2- ((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile. LCMS-ESI+ (m/z): [M+H]+ calcd for C35H33N504S: 620.7; found: 620.2

References: [1]Patent: WO2015/187684,2015,A1 .Location in patent: Page/Page column 117.

10
[ 912369-50-7 ]
[ 1247001-86-0 ]
[ 1247002-57-8 ]