[ CAS No. 179942-45-1 ] (6-((tert-Butyldimethylsilyl)oxy)naphthalen-2-yl)boronic acid

Cat. No.: A393687

2D 3D

Structure of 179942-45-1 * Storage: Inert atmosphere,Room Temperature

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Quality Control of [ 179942-45-1 ]

COA NMR CNMR HPLC LC-MS

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Specification

Alternatived Products of [ 179942-45-1 ]

Product Details of [ 179942-45-1 ]

CAS No. :	179942-45-1	MDL No. :	MFCD04115644
Formula :	C₁₆H₂₃BO₃Si	Boiling Point :	-
Linear Structure Formula :	(CH₃)₃CSi(CH₃)₂OC₁₀H₆B(OH)₂	InChI Key :	QJXUSWJSQVIBCP-UHFFFAOYSA-N
M.W :	302.25	Pubchem ID :	3756084
Synonyms :

Safety of [ 179942-45-1 ]

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

Application In Synthesis of [ 179942-45-1 ]

* 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 [ 179942-45-1 ]

[ 179942-45-1 ] Synthesis Path-Downstream 1~22

1
[ 179942-45-1 ]
[ 137396-01-1 ]
[ 550998-18-0 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3953 - 3979

2
[ 100751-65-3 ]
[ 179942-45-1 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3953 - 3979
[2]Patent: WO2008/124812,2008,A1

3
[ 179942-45-1 ]
6-(4-hydroxy-2-methoxyphenyl)-2-naphthol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3953 - 3979

4
[ 15231-91-1 ]
[ 179942-45-1 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3953 - 3979
[2]Patent: WO2008/124812,2008,A1

5
[ 18162-48-6 ]
MeHal [ No CAS ]
[ 179942-45-1 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3953 - 3979

7
[ 179942-45-1 ]
[ 636-98-6 ]
C₂₂H₂₅NO₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; at 100℃; for 2h;	6-(4-nitrophenyl)naphthalen-2-ol (9)Sodium carbonate (112 mg, 1.06 mmol) in water (5 ml) was added to a solution of 8 (320 mg, 1.06 mmol), para-iodonitrobenzene (264 mg, 1.06 mmol) and Pd(PPh3 )4 (66 mg, 0.053 mmol) in toluene (10 ml). The reaction mixture was degassed by bubbling nitrogen for 10 min and then heated to 100 0C for 2 h. After cooling down to the room temperature, ethyl acetate and water was added. The organic layer was separated, washed with brine dried with anhydrous sodium sulfate and evaporated. The residue (470 mg) was dissolved in THF (20 ml) and TBAF (IM in THF, 6 ml) was added. After stirring at the room temperature for 3 h, the reaction mixture was poured in to water and extracted with ethyl acetate. Organic layer was washed with brine, dried with sodium sulfate and evaporated. The residue was purified by Biotage Flash column chromatography (10 % hexane in dichloromethane as the eluant) to obtain product 9 (230 mg, Y: 81.8%) as an orange solid. 1H NMR (CDCl3): δ 8.25 (2H, d, J= 7.0 Hz), 7.95 (IH, m), 7.75 (4H, M), 7.61(1H, d, d, J1 = 8.6 Hz, J2 = 1.8 Hz), 7.11 (2H, m). HRMS (EI) m/z calcd. for [Ci6HiiNO3]+ 265.0739, found 265.0755

Reference： [1]Patent: WO2008/124812,2008,A1 .Location in patent: Page/Page column 49

8
[ 179942-45-1 ]
[ 937701-59-2 ]
C₂₈H₃₇FO₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium carbonate;tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; In ethanol; toluene; at 100℃;	6-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)phenyl)naphthalen-2-ol (28)Palladium tetrakis(triphenylphosphine) (11.6 mg, 0.01 mmol) was added to a solution of compound 27 (71 mg, 0.2 mmol), 2 (60 mg, 0.2 mmol) and tetrabutylammonium bromide (5 mg, 0.015 mmol) in Toluene (5 ml) and Ethanol (2 ml). The solution was degassed by bubbling <n="61"/>nitrogen for 10 min. A pre-degassed solution of sodium carbonate (2M, aq, 1 ml) was then added. Under the nitrogen atmosphere, the reaction mixture was heated at 100 0C overnight. The mixture was then cooled down to room temperature. Ethyl acetate and water was added. Organic layer was separated, washed with brine, dried over sodium sulfate and evaporated. The residue was dissolved in THF (4 ml), TBAF (IM in THF, ImI) was added slowly. Reaction mixture was stirred at room temperature for 3 h. Solvent was removed by vacuum. Residue was purified by PTLC (45 % ethyl acetate in hexane as the developing solvent) to obtain product 28 (50.7 mg, Y: 68.5 %). 1H NMR (CDCl3): δ 7.88 (IH, br), 7.73 (2H, m), 7.60 (3H, m), 7.12 (2H, m), 6.97 (2H, d, J= 8.8 Hz), 5.34 (IH, br), 4.58 (2H, d, t, Ji = 47.8 Hz, J2 = 4.2 Hz), 4.17 (2H, t, J= 4.8 Hz), 3.83 (8H, m). HRMS (EI) m/z calcd. for [C22H23FO4]+ 370.1580, found 370.1574.

Reference： [1]Patent: WO2008/124812,2008,A1 .Location in patent: Page/Page column 59-60

9
C₂₂H₃₅BO₃Si [ No CAS ]
[ 179942-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In tetrahydrofuran;Acidic conditions;	6-(ter*-butyldimethylsilyloxy)naphthalen-2-ylboronic acid (8)A solution of compound 7 (674 mg, 2 mmol) in anhydrous THF (15 ml) was cooled to - 78 0C. n-Butyl lithium (1.6 M, 1.88 ml) was added dropwise within 30 minutes and the reaction mixture was stirred at -78 0C for 20 min. Triisopropyl borate (1.13 g, 6 mmol) was then added and the reaction mixture was stirred at -78 0C for another 20 min and then allowed to warm up to room temperature. IN HCl was added until water layer became acidic. Ethyl acetate was added and organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated. Residue was applied on Biotage Flash column chromatography (1% methanol in dichloromethane as the eluant) to obtain product 8 (320 mg, 53 %), 1H NMR (CDCl3): δ 8.75 (IH, m), 8.24 (IH, d, J= 8.2 Hz), 7.95 (IH, d, J= 8.8 Hz), 7.81 (IH, d, J= 8.2 Hz), 7.16 (2H, m), 1.05 (9H, s), 0.27 (6H, s).

Reference： [1]Patent: WO2008/124812,2008,A1 .Location in patent: Page/Page column 49

10
[ 179942-45-1 ]
[ 32779-37-6 ]
[ 1261072-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 16h;Inert atmosphere; sealed tube;	To a stirred solution of 2,5 dibromo pyrimidine (0.32 g, 1.332 mmol), obtained from Preparation 44, in toluene (6 imL) was added 6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-2-yl-boronic acid (0.48 g, 1.585 mmol), EtOH (2 ml_), water (1 ml_) and Na2CO3 (0.35 g, 3.33 mmol). Argon was bubbled through the reaction mixture for 30 minutes. Then Pd(PPh3)4 (0.075 g, 0.065 mmol) was added and the mixture was heated in a sealed tube at 90 0C for 16 hours. The solvent was evaporated under vacuum and the reaction mixture was diluted with ethyl acetate (15 ml_). The ethyl acetate layer was filtered through celite then washed with water (10 ml_) and brine (10 ml_). It was then dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silica gel by using ethyl acetate : hexane (1 :9) mixture to give the title compound as a white solid (546 mg).1H NMR (400 MHz, CDCI3): δ= 8.86 (s, 1 H), 8.83 (s, 1 H), 8.40 (d, 1 H), 7.87 (d, 1 H), 7.76 (d, 1 H), 7.31 (s, 1 H), 7.20 (s, 1 H), 7.10 (dd, 1 H), 1.02 (s, 9H), 0.26 (s, 6H). LCMS (System 1 ) (run time = 5 min): Rt = 3.57 min; m/z 415; 417 [M+H]+

Reference： [1]Patent: WO2011/4276,2011,A1 .Location in patent: Page/Page column 116

11
[ 179942-45-1 ]
[ 624-28-2 ]
[ 1261071-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 16h;Inert atmosphere; sealed tube;	To a stirred solution of 2,5-dibromo pyridine (0.5 g, 2.11 mmol) in toluene (18 ml_) was added 6-(tert-butyl- dimethyl-silanyloxy)-naphthalen-2-yl-boronic acid (0.765 g, 2.52 mmol), ethanol (6 ml_), water (4 ml_) and Na2CO3 (0.671 g, 6.33 mmol). Argon was bubbled through the reaction mixture for 30 minutes. ThenPd(PPh3)4 (0.121 g, 0.104 mmol) was added and the mixture was heated in a sealed tube at 900C for 16 hours. The solvent was evaporated under vacuum and the residue was diluted with ethyl acetate (25 ml_). The reaction mixture was filtered through celite. The organic layer was washed with water (15 ml_) followed by brine (15 ml_), dried over Na2SO4 and was evaporated to dryness. The crude mass was purified by column chromatography on silica gel by using ethyl acetate : hexane (1 :9) mixture to afford the title compound as a white solid (300 mg).1H NMR (400 MHz, CDCI3): δ= 8.75 (1 H, s), 8.37 (1 H, s), 8.04 (1 H, m), 7.88 (1 H, m), 7.80 (1 H, m), 7.74 (1 H, m), 7.20 (1 H, s), 7.11 (1 H, m), 1.02 (9H, s), 0.26 (6H, s). LCMS (System 1 ) (run time = 5 min): R4 = 3.46 min; 414; 416 [M+H]+

Reference： [1]Patent: WO2011/4276,2011,A1 .Location in patent: Page/Page column 112

12
[ 179942-45-1 ]
[ 19745-07-4 ]
[ 1261072-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 45℃; for 2h;Inert atmosphere;	To a stirred solution of <strong>[19745-07-4]2,5-dichloro-pyrazine</strong> (0.5 g, 3.37 mmol) in toluene (10 ml_) was added 6-(tert-butyl- dimethyl-silanyloxy)-naphthalen-2-yl-boronic acid (1.02 g, 3.37 mmol), EtOH (10 ml_), water (2 ml_) and NaHCO3 (0.42 g, 5.0 mmol). Argon was bubbled through the reaction mixture for 30 min. Then Pd(PPh3)4 (0.19 g, 0.16 mmol) was added and the mixture was heated at 45°C for 2 hours. The EtOH was evaporated under vacuum and the mixture was diluted with ethyl acetate (35 ml_). The reaction mixture was then filtered through celite. The organic layer was washed with water (1 x 10 ml_), and brine (1 x 10 ml_), then dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silica gel (ethyl acetate: hexane, 1 :19) to afford the title compound as a white solid (450 mg). 1H NMR (400 MHz, DMSO-d6): delta= 0.28 (6H, s), 1.00 (9H, s), 7.20 (1 H, d), 7.38 (1 H, s), 7.99 (2H, m), 8.17 (1 H, m), 8.70 (1 H, s), 8.75 (1 H, s), 9.40 (1 H, s). LCMS (System 1 ) (run time = 5 min): Rt = 3.45 min, 371 [M+H]+

Reference： [1]Patent: WO2011/4276,2011,A1 .Location in patent: Page/Page column 147; 148

13
[ 179942-45-1 ]
[ 1261071-96-8 ]

Reference： [1]Patent: WO2011/4276,2011,A1

14
[ 179942-45-1 ]
[ 1261071-97-9 ]

Reference： [1]Patent: WO2011/4276,2011,A1

15
[ 179942-45-1 ]
[ 1261071-98-0 ]

Reference： [1]Patent: WO2011/4276,2011,A1

16
[ 179942-45-1 ]
[ 1261071-99-1 ]

Reference： [1]Patent: WO2011/4276,2011,A1

17
[ 179942-45-1 ]
5-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-2-(6-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}naphthalen-2-yl)pyridine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2011/4276,2011,A1

18
[ 179942-45-1 ]
[ 1228552-74-6 ]

Reference： [1]Patent: WO2011/4276,2011,A1

19
[ 179942-45-1 ]
[ 1261072-44-9 ]

Reference： [1]Patent: WO2011/4276,2011,A1

20
[ 179942-45-1 ]
[ 1261072-45-0 ]

Reference： [1]Patent: WO2011/4276,2011,A1

21
[ 179942-45-1 ]
[ 1261072-46-1 ]

Reference： [1]Patent: WO2011/4276,2011,A1

22
[ 179942-45-1 ]
2-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}-5-(6-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}naphthalen-2-yl)pyrazine tetrahydrochloride [ No CAS ]

Reference： [1]Patent: WO2011/4276,2011,A1

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Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

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[ CAS No. 179942-45-1 ] (6-((tert-Butyldimethylsilyl)oxy)naphthalen-2-yl)boronic acid

Quality Control of [ 179942-45-1 ]

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Safety of [ 179942-45-1 ]

Application In Synthesis of [ 179942-45-1 ]

[ 179942-45-1 ] Synthesis Path-Downstream 1~22

Technical Information

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Prevention

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