128733-85-7|(5-(tert-Butyl)-2-methoxyphenyl)boronic acid| Ambeed

CAS No. :	128733-85-7
Formula :	C₁₁H₁₇BO₃
M.W :	208.06
SMILES Code :	COC1=C(C=C(C=C1)C(C)(C)C)B(O)O
MDL No. :	MFCD06201034
InChI Key :	LXFOJKCQSAYVMF-UHFFFAOYSA-N
Pubchem ID :	14740579

Safety of [ 128733-85-7 ]

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

Application In Synthesis of [ 128733-85-7 ]

* 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 [ 128733-85-7 ]

[ 128733-85-7 ] Synthesis Path-Downstream 1~51

1
[ 128733-84-6 ]
[ 128733-85-7 ]
[ 128733-86-8 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4622 - 4634.

2
[ 128733-85-7 ]
[ 132268-08-7 ]
5,5',5''-Tri-tert-butyl-2,2',2''-trimethoxy-[1,1';3',1'']terphenyl [ No CAS ]

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 138 - 144.

3
[ 610-97-9 ]
[ 128733-85-7 ]
5'-<i>tert</i>-butyl-2'-methoxy-biphenyl-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 3849 - 3853.

4
[ 38303-36-5 ]
[ 128733-85-7 ]
[ 916747-36-9 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9080 - 9087.

5
[ 128-63-2 ]
[ 128733-85-7 ]
1,3,6,8-tetrakis(5-tert-butyl-2-methoxyphenyl)pyrene [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9080 - 9087.

6
[ 128733-85-7 ]
[ 916747-40-5 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9080 - 9087.

7
[ 128733-85-7 ]
[ 916747-44-9 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9080 - 9087.

8
[ 128733-85-7 ]
2-tert-butyldibenzo<b,d>pyran-6-one [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 3849 - 3853.

9
[ 944280-22-2 ]
[ 128733-85-7 ]
(4S,6S)-6-[3,5-bis(trifluoromethyl)phenyl]-3-[5'-tert-butyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazinan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In tetrahydrofuran; water; at 80℃; for 1.5h;	(4S,65)-6-[3,5-bis(txifluorornethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-l,3-oxazinan- 2-one (Intermediate 23; 25 mg; 0.041 mmol), (5-rer.-butyl-2-methoxyphenyl)boronic acid (11.1 mg; 0.053 nxmol), l-l '-bis(di /erf-butylphosphino)ferrocene palladium dichloride (2.7 mg; 0.0041 mrnol), 1 N K2CO3 (1.2 mL) and THF (1.2 mL) were combined in a sealed tube and heated at 80C for 1.5 h. The reaction was diluted with H2O (10 mL) and extracted with EtOAc (3 x 10 mL). The combined extracts were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-30% EtOAc/hexanes gradient) to afford (45,6-S)-6-[3,5- bis(trifluoromethyl)phenyl]-3-[5'-te/-/-butyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4- methyl-l,3-oxazinan-2-one as a white solid. LCMS = 648.0 (M+l)+. lH NMR (CDCl3, 500 MHz, mixture of atropisomers): 5 7.86-7.83 (m, 2 H), 7.78 (s, 1 H), 7.68 (s, 1 H), 7.63-7.59 (m, 1 H), 7.44-7.36 (m, 2 H), 7.18 (dd, J = 6.7, 2.4 Hz, 1 H), 6.94 (d, J= 8.7 Hz5 1 H), 5.20 (d, J= 16 Hz, 1 H), 5.16 (d, J = 11.2 Hz, 1 H), 4.38 (d, J= 15.8 Hz, 1 H), 3.80 (s, 3 H), 3.41-3.34 (m, 1 H), 2.29-2.24 (m, 1 H), 1.88-1.81 (m, 1 H), 1.32 (s, 9 H), 1.02 (d, J= 6.2 Hz, 3 H).

References: [1]Patent: WO2007/81570,2007,A2 .Location in patent: Page/Page column 63.

10
[ 75060-39-8 ]
[ 128733-85-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4-tert-butyl-2-iodo-l-methoxybenzene (0.164 g, 0.56 mmol) in dry THF (5 mL) at -78 0C, M-butyl lithium (0.27 mL, 0.68 mmol, 2.5 M) was added. The solution was stirred at -78 0C for 30 min. Trimethyl borate (0.19 mL, 1.70 mmol) was added. The solution was stirred at -780C for 3 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3 x 15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent.

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.
[2]Patent: WO2007/81569,2007,A2 .Location in patent: Page/Page column 38.

11
[ 34160-40-2 ]
[ 128733-85-7 ]
[ 866613-68-5 ]

References: [1]Tetrahedron,2008,vol. 64,p. 9857 - 9864.
[2]Organometallics,2013,vol. 32,p. 249 - 259.

12
[ 934842-20-3 ]
[ 128733-85-7 ]
C₃₀H₂₈F₉NO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7469 - 7472.

13
[ 49669-22-9 ]
[ 128733-85-7 ]
[ 1332625-70-3 ]

References: [1]Dalton Transactions,2011,vol. 40,p. 8507 - 8509.

14
[ 128733-85-7 ]
C₆₄H₅₈N₄O₄ [ No CAS ]

References: [1]Dalton Transactions,2011,vol. 40,p. 8507 - 8509.

15
[ 128733-85-7 ]
C₆₀H₅₀N₄O₄ [ No CAS ]

References: [1]Dalton Transactions,2011,vol. 40,p. 8507 - 8509.

16
[ 128733-85-7 ]
[ 1332625-71-4 ]

References: [1]Dalton Transactions,2011,vol. 40,p. 8507 - 8509.

17
[ 128733-85-7 ]
[ 1332625-72-5 ]

References: [1]Dalton Transactions,2011,vol. 40,p. 8507 - 8509.

18
[ 128733-85-7 ]
[ 107-02-8 ]
[ 1339074-98-4 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 8986 - 8998.

19
[ 5396-38-3 ]
[ 128733-85-7 ]

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.
[2]Patent: WO2007/81569,2007,A2 .

20
[ 128733-85-7 ]
[ 1379680-58-6 ]

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.

21
[ 128733-85-7 ]
[ 1379680-59-7 ]

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.

22
[ 128733-85-7 ]
[ 1379680-60-0 ]

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.

23
[ 128733-85-7 ]
[ 22385-96-2 ]

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.

24
[ 128733-85-7 ]
[ 75060-39-8 ]
[ 133373-15-6 ]

References: [1]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 201 - 208.

25
[ 16400-51-4 ]
[ 128733-85-7 ]
[ 1374794-16-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; for 72h;Inert atmosphere;	1.1.1. 4merMe. A mixture of 3,3'-dibromo-1,1'-biphenyl (7.00 g, 22.4 mmol), 5-tert-butyl-2-methoxyphenylboronic acid (10.4 g, 49.9 mmol), and Pd(PPh3)4 (259 mg, 0.224 mmol) in toluene (200 mL) and 2 M aq. K2CO3 (200 mL) was stirred at 100 C for 3 days under N2. The mixture was then extracted with EtOAc (3x200 mL). The organic layer was washed with H2O (200 mL) and brine (200 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (SiO2 (400 g), n-hexane/EtOAc=100/1 to 20/1 (v/v)) to give 4merMe as a white solid in 98% yield.

References: [1]Tetrahedron,2012,vol. 68,p. 4470 - 4478.

26
[ 128733-85-7 ]
[ 866613-67-4 ]

References: [1]Organometallics,2013,vol. 32,p. 249 - 259.

27
[ 128733-85-7 ]
[ 866613-69-6 ]

References: [1]Organometallics,2013,vol. 32,p. 249 - 259.

28
[ 626-39-1 ]
[ 128733-85-7 ]
[ 1422465-68-6 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 2266 - 2274.

29
[ 626-39-1 ]
[ 128733-85-7 ]
[ 1422465-69-7 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 2266 - 2274.

30
[ 128733-85-7 ]
6-(5-tert-butyl-2-methoxyphenyl)-6′-(tributylstannyl)-2,2′-bipyridine [ No CAS ]

References: [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986.

31
[ 128733-85-7 ]
6,6′-bis(3-bromo-5-tert-butyl-2-methoxyphenyl)-2,2′-bipyridine [ No CAS ]

References: [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986.

32
[ 49669-22-9 ]
[ 128733-85-7 ]
[ 1332625-70-3 ]
6-bromo-6′-(2-methoxy-5-methylphenyl)-2,2′-bipyridine [ No CAS ]

References: [1]Dalton Transactions,2013,vol. 42,p. 15974 - 15986.

33
[ 98-54-4 ]
[ 128733-85-7 ]

References: [1]Patent: US2014/135320,2014,A1 .

34
[ 2198-66-5 ]
[ 128733-85-7 ]

References: [1]Patent: US2014/135320,2014,A1 .

35
[ 3510-66-5 ]
[ 128733-85-7 ]
[ 1609654-41-2 ]

Yield	Reaction Conditions	Operation in experiment
99%		A mixture of 2-bromo-5-methylpyridine [purchased from TCI] (0.827 g, 4.81 mmol), <strong>[128733-85-7](5-(tert-butyl)-2-methoxyphenyl)boronic acid</strong> [Intermediate 5] (1.2 g, 5.77 mmol) and potassium carbonate (0.997 g, 7.21 mmol) in dimethoxyethane (15 mL) and water (5 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (277.8 mg, 0.24 mmol) was added and the reaction mixture heated to 80 C. in a sealed vial for 22 hours. The cooled reaction mixture was partitioned between ethyl acetate (80 mL) and 1 M aqueous sodium hydroxide solution (80 mL), the organic phase separated, washed with water (80 mL) and saturated brine (80 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a yellow syrup. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 35% ethyl acetate in hexanes to give 2-(5-(tert-butyl)-2-methoxyphenyl)-5-methylpyridine (1.216 g, 99% yield) as a colorless oil. HPLC/MS Rt=2.58 min, m/z 256.1 (M+H+).

References: [1]Patent: US2014/135320,2014,A1 .Location in patent: Paragraph 0328; 0329.

36
[ 128733-85-7 ]
[ 1609654-42-3 ]

References: [1]Patent: US2014/135320,2014,A1 .

37
[ 5419-55-6 ]
[ 41280-65-3 ]
[ 128733-85-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0℃; for 4.5h;Inert atmosphere;	n-Butyllithium in hexane (2.5 M, 18.1 mL, 45.24 mmol) was added dropwise to a solution of 2-bromo-4-(tert-butyl)-1-methoxybenzene (10.0 g, 41.13 mmol) and triisopropyl borate (11.39 mL, 49.35 mmol) in tetrahydrofuran (90 mL) at -78 C. under nitrogen. The reaction mixture was stirred at -78 C. for 3 hours then allowed to warm slowly to 0 C. over 90 minutes. The reaction was then quenched by the addition of water (90 mL) and the tetrahydrofuran removed under reduced pressure. The resulting aqueous suspension was partitioned between diethyl ether (80 mL) and 1.0 M aqueous sodium hydroxide solution (100 mL). The aqueous phase was separated, cooled to 0 C. then acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was stood at 0 C. for 15 minutes then filtered washing the solid product with water and cold hexane to give (5-(tert-butyl)-2-methoxyphenyl)boronic acid (6.349 g, 74% yield) as a white crystalline solid. HPLC/MS Rt=5.04 min, m/z 209.1 (M+H+).
74%	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 3h;Inert atmosphere;	n-Butyllithium in hexane (2.5 M, 18.1 mL, 45.24 mmol) was added dropwise to a solution of 2-bromo-4-(tert-butyl)-1-methoxybenzene (10.0 g, 41.13 mmol) and triisopropyl borate (11.39 mL, 49.35 mmol) in tetrahydrofuran (90 mL) at -78 C. under nitrogen. The reaction mixture was stirred at -78 C. for 3 hours then allowed to warm slowly to 0 C. over 90 minutes. The reaction was then quenched by the addition of water (90 mL) and the tetrahydrofuran removed under reduced pressure. The resulting aqueous suspension was partitioned between diethyl ether (80 mL) and 1.0 M aqueous sodium hydroxide solution (100 mL). The aqueous phase was separated, cooled to 0 C. then acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was stood at 0 C. for 15 minutes then filtered washing the solid product with water and cold hexane to give (5-(tert-butyl)-2-methoxyphenyl)boronic acid (6.349 g, 74% yield) as a white crystalline solid. [0157] HPLC/MS Rt=5.04 min, m/z 209.1 (M+H+).

References: [1]Patent: US2014/135320,2014,A1 .Location in patent: Paragraph 0241; 0242.
[2]Patent: US2014/135360,2014,A1 .Location in patent: Paragraph 0156.

38
[ 1609573-33-2 ]
[ 128733-85-7 ]

References: [1]Patent: US2014/135360,2014,A1 .

39
[ 583-55-1 ]
[ 128733-85-7 ]
C₁₇H₁₉BrO [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 3061 - 3064.

40
[ 128733-85-7 ]
3-(tert-butyl)-2′,3′-diphenylspiro[cyclohexa[2,4]diene-1,1′-inden]-6-one [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 3061 - 3064.

41
[ 128733-85-7 ]
1-bromo-4-(5-tert-butyl-2-hydroxyphenyl)naphthalene [ No CAS ]