243990-54-7|(3-(Benzyloxy)-4-methoxyphenyl)boronic acid| Ambeed

CAS No. :	243990-54-7
Formula :	C₁₄H₁₅BO₄
M.W :	258.08
SMILES Code :	COC1=C(OCC2=CC=CC=C2)C=C(C=C1)B(O)O
MDL No. :	MFCD09027252
InChI Key :	GKHSIZCQILKQCU-UHFFFAOYSA-N
Pubchem ID :	10587276

Safety of [ 243990-54-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 243990-54-7 ]

* 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 [ 243990-54-7 ]

[ 243990-54-7 ] Synthesis Path-Downstream 1~41

1
[ 185418-17-1 ]
[ 243990-54-7 ]
[ 243990-60-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5437 - 5444.
[2]Synthetic Communications,1999,vol. 29,p. 2719 - 2730.

2
diisopropyl 3-benzyloxy-4-methoxyphenylboronate [ No CAS ]
[ 243990-54-7 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 2719 - 2730.

3
[ 243990-54-7 ]
[ 265981-13-3 ]
3-(3-benzyloxy-4-methoxy-phenyl)-2-bromo-pyridine [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.

4
[ 243990-54-7 ]
[ 265981-13-3 ]
2-(3-benzyloxy-4-methoxy-phenyl)-3-iodo-pyridine [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.

5
[ 243990-54-7 ]
[ 635682-35-8 ]
4-(3'-benzyloxy-4'-methoxyphenyl)-5,6,7-trimethoxychromen-2-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5437 - 5444.

6
2-(benzyloxy)-4-iodo-1-methoxybenzene [ No CAS ]
[ 243990-54-7 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 723 - 736.

7
[ 243990-54-7 ]
[ 847063-30-3 ]
[ 847063-31-4 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 723 - 736.

8
[ 243990-54-7 ]
2-methoxy-5-[3-(3,4,5-trimethoxy-phenyl)-pyridin-2-yl]-phenol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 723 - 736.
[2]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.

9
[ 243990-54-7 ]
[ 88126-45-8 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5437 - 5444.
[2]Synthetic Communications,1999,vol. 29,p. 2719 - 2730.

10
[ 243990-54-7 ]
[ 566915-68-2 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.

11
[ 243990-54-7 ]
[ 847063-31-4 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.

12
[ 243990-54-7 ]
3-(3-benzyloxy-4-methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-pyridine [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.

13
[ 78504-28-6 ]
[ 243990-54-7 ]

Yield	Reaction Conditions	Operation in experiment
		[311.2] 4.86 g of 2-Benzyloxy-4-bromo-1-methoxybenzene was dissolved in 100 ml of anhydrous tetrahydrofuran and cooled to -78C in a nitrogen atmosphere. 15 ml of 1.6 M n-butyl lithium in hexane was added dropwise, and the mixture was stirred for 30 minutes. 6 ml of Triisopropoxy borate was added all at once, and the mixture was allowed to warm overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was dissolved in 1N aqueous sodium hydroxide and extracted with diethyl ether. The aqueous layer was neutralized with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated to give 1.76 of the title compound.1H-NMR(CDCl3) δ: 3.76 (s, 3H) 5.04 (s, 2H) 6.93 (d, J=8.0Hz, 1H) 7.31-7.46 (m, 6H) 7.86 (s, 1H)

References: [1]Synthetic Communications,1999,vol. 29,p. 2719 - 2730.
[2]Patent: EP1394147,2004,A1 .Location in patent: Page 179.
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

14
[ 243990-54-7 ]
2-(3-benzyloxy-4-methoxy-phenyl)-4-methyl-[1,3,2]dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In propylen glycol; diethyl ether; at 20℃; for 1h;	[312.1] 1.753 g of 2-Benzyloxy-1-methoxybenzeneboronic acid was suspended in 50 ml of diethyl ether, and 0.49 ml of propylene glycol was added thereto. The mixture was stirred at room temperature for 1 hour, and the solvent was removed to give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane. This product was dissolved in 30 ml of 1,2-dimethoxyethane, then 1.5 g of potassium carbonate, 1. 9 g of methyl 3-bromophenylacetate and 270 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred at 80C for 3 hours in a nitrogen atmosphere. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 1.356 g of the title compound in the 6:1→4:1 fraction.1H-NMR(CDCl3) δ: 3.67 (s, 2H) 3.70 (s, 3H) 3.92 (s, 3H) 5.21 (s, 2H) 6.96 (d, J=8.8Hz, 1H) 7.15 (dd, J=2.4, 8.8Hz, 1H) 7.22 (dt, J=2.4, 7.2 Hz, 1H) 7.33 (t, J=7.6Hz, 1H) 7.36-7.40 (m, 5H) 7.48 (d, J=8.4Hz, 1H)

References: [1]Patent: EP1394147,2004,A1 .Location in patent: Page 180.

15
[ 1200639-25-3 ]
[ 243990-54-7 ]
[ 1200639-48-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7783 - 7788.

16
[ 243990-54-7 ]
4-(3'-hydroxy-4'-methoxyphenyl)-7-methoxycoumarin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

17
[ 243990-54-7 ]
[ 622864-48-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

18
[ 243990-54-7 ]
[ 1292297-03-0 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

19
[ 243990-54-7 ]
[ 1292297-04-1 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

20
[ 243990-54-7 ]
[ 1292297-05-2 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

21
[ 243990-54-7 ]
[ 1292297-06-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

22
[ 243990-54-7 ]
[ 1292297-07-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

23
[ 243990-54-7 ]
4-(3'-hydroxy-4'-methoxyphenyl)-5,6,7-trimethoxycoumarin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3153 - 3162.

24
[ 1610520-99-4 ]
[ 243990-54-7 ]
[ 1610520-83-6 ]

Yield	Reaction Conditions	Operation in experiment
3.2 mg	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate; In isopropyl alcohol; at 110℃; for 0.333333h;Microwave irradiation;	To a solution of (S)-ferf-butyl 4-((7-bromo-5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]pyridin-2- yl)methyl)-3-methylpiperazine-1-carboxylate (for a preparation see Intermediate 84, 22 mg, 0.048 mmol) and (3-(benzyloxy)-4-methoxyphenyl)boronic acid (18.66 mg, 0.072 mmol) in isopropanol (2 ml.) were successively added potassium carbonate (0.121 ml_, 0.241 mmol) and PEPPSI (3.28 mg, 4.82 μιτιοΙ). The reaction mixture was heated in a microwave reactor at 1 10 C for 20 min and was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was diluted in a 1 : 1 MeOH/DMSO mixture (1 ml.) and purified via MDAP. The appropriate fractions were combined and concentrated in vacuo to give a residue which was diluted in a 1 :1 MeOH/DMSO mixture (1 ml.) and further purified via MDAP. The appropriate fractions were collected and concentrated in vacuo to give (S)-ferf-butyl-4-((7-(3-(benzyloxy)-4-methoxyphenyl)-5- methyl-4-oxo-4,5-dihydrothieno[3,2-c]pyridin-2-yl)methyl)-3-methylpi (3.2 mg) as a viscous yellow oil. LCMS (2 min, High pH): Rt = 1.40 min, MH+ = 590

References: [1]Patent: WO2014/78257,2014,A1 .Location in patent: Page/Page column 103; 104.

25
[ 1444006-14-7 ]
[ 243990-54-7 ]
[ 1444006-15-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; for 15h;Inert atmosphere; Reflux;	General procedure: The mixture of compound 3 (10g, 57.5mmol), Pd(PPh3)4 (100mg, 0.09mmol), K2CO3 (18.2g, 0.132mol) and 3,4,5-trimethoxyphenylboronic acid (14.6g, 68.9mmol) in DMF (50mL) was refluxed under N2 (g) for 15h. After cooled to room temperature, the mixture was quenched with water (250mL), extracted with CH2Cl2 (100×3mL), and evaporated to dryness to give a crude product, which was purified by column chromatography to give 5 as a white solid (11.5g, 76% yield).

References: [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 613 - 620.

26
[ 1111111-13-7 ]
[ 243990-54-7 ]
[ 1444006-28-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With pyridine; pyridine N-oxide; copper diacetate; In dichloromethane; at 20℃;Molecular sieve;	General procedure: A mixture of 6-bromopyridin-2(1H)-one (3) (8.3g, 47.7mmol), (3,4,5-trimethoxyphenyl)boronic acid (20.1g, 94.8mmol), Cu(OAc)2 (0.9g, 5.0mmol), pyridine (7.7mL, 94.8mmol), pyridine-N-oxide (5.0g, 52.6mmol), 4ÅMS (2.0g) in dry CH2Cl2 (100mL) was stirred at room temperature overnight. Then CH2Cl2 (300mL) and NH3.H2O (50mL) were added, and the reaction mixture was filtered through Celite. The filtrate was washed with water, dried over Na2SO4, and evaporated to dryness to yield the crude product, which was triturated with CH2Cl2 (50mL) to give compound 4 as a white solid (13.0g, 77% yield).

References: [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 613 - 620.

27
[ 1642785-09-8 ]
[ 243990-54-7 ]
[ 1642784-52-8 ]

References: [1]Acta Pharmacologica Sinica,2014,vol. 35,p. 916 - 928.

28
[ 100-39-0 ]
[ 243990-54-7 ]