Name: 259209-17-1|(2-Hydroxy-3-methoxyphenyl)boronic acid|96%
Brand: Ambeed
SKU: A194458
Rating: 97 (40 reviews)

1
[ 259209-52-4 ]
[ 259209-17-1 ]
6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		II.50 50 50 Prepration of 6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine 6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine was prepared from 6-bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine and 2-hydroxy-3-methoxyphenylboronic acid in 33% yield using method F; δH [2H6]-DMSO 13.52,(2H, b), 8.31,(2H, dd), 8.26,(1H, d), 8.21,(1H, d), 8.12,(1H, d), 8.02,(1H, d), 7.70,(1H, d), 7.09,(1H, d), 6.92, (1H, t), 6.82,(1H, d), 3.86,(3H, s), 2.32,(3H, s); MS 385 (MH)+; HPLC retention time (system 1) 4.21 minutes.

Reference： [1]Current Patent Assignee: MINDSET RX INC - US6177419, 2001, B1

2
[ 259209-17-1 ]
[ 1272672-24-8 ]
[ 1272672-25-9 ]

Yield	Reaction Conditions	Operation in experiment
28.3%	With caesium carbonate In 1,4-dioxane; water at 160℃; for 0.666667h; microwave reactor;	24 To a solution of 1 -(4-bromophenyl)-2-chloro-7-hydroxy-5-oxo-4,5-dihydro-1 H- pyrrolo[3,2-b]pyridine-6-carbonitrile (Example 23) (150 mg, 0.41 1 mmol) in 1 ,4- dioxane (5 mL)/ water (3 ml.) were added [2-hydroxy-3-(methyloxy)phenyl]boronic acid (83 mg, 0.494 mmol), cesium carbonate (402 mg, 1.234 mmol) and Pd(PPh3)4 (1.0 mg, 1 .234 μηηοΙ). The reaction vessel was sealed and heated to 160 °C for 20 min in a microwave reactor. To complete the reaction, [2-hydroxy-3- (methyloxy)phenyl]boronic acid (83 mg, 0.494 mmol) and Pd(PPh3)4 (1.0 mg, 1.234 μηηοΙ) were added again and the reaction vessel was sealed and heated to 160 °C for 20 min in microwave reactor. After cooling, the reaction mixture was extracted, and the organic layer was washed with 1 N HCI solution and evaporated off. The residue was dissolved with a hot MeOH /CH3CN (80/20) mixture and treated with charcoal filtered. The filtrate was crystallined to give the product 2-chloro-7-hydroxy-1-[2'- hydroxy-3'-(methyloxy)-4-biphenylyl]-5-oxo-4,5-dihydro-1 H-pyrrolo[3,2-b]pyridine-6- carbonitrile (50 mg, 0.1 16 mmol, 28.3 % yield) as a white powder. 1H NMR: (DMSO- d6, 300MHz) δ 9.74 (br s, 1 H), 8.71 (s, 1 H), 7.56 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 8.4 Hz, 2H), 7.02-6.84 (m, 3H), 5.94 (s, 1 H), 3.86 (s, 3H). LCMS: (M+H)+ : 408; Rt: 2.63 min. HRMS: calculated for C2iH15CIN304 (M+H)+ : 408.0751 ; found: 408.0765; Rt: 2.34 min.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/29855, 2011, A1 Location in patent: Page/Page column 118

3
[ 259209-17-1 ]
[ 1346608-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / Reflux 2.1: dichloromethane / 3 h / 20 °C 2.2: 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

4
[ 259209-17-1 ]
[ 1346608-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / Reflux 2.1: dichloromethane / 3 h / 20 °C 2.2: 80 °C 3.1: ethanol; sodium / 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

5
[ 259209-17-1 ]
[ 1346606-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 80 °C 3: sodium / ethanol / 2 h / 90 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

6
[ 259209-17-1 ]
[ 1346607-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 90 °C 2.2: 72 h / 50 °C 3.1: sodium hydroxide / ethanol / 90 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

7
[ 259209-17-1 ]
[ 1346606-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: xylene / 0.25 h / 140 °C / microwave irradiation 3: ethanol; sodium / 1.5 h / Reflux

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

8
[ 259209-17-1 ]
[ 1346607-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 80 °C 3: sodium / ethanol / 2 h / 90 °C 4: HATU / dichloromethane; tetrahydrofuran / 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

9
[ 259209-17-1 ]
[ 1346607-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 80 °C 3: sodium / ethanol / 2 h / 90 °C 4: hydrogenchloride / 4 h / 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

10
[ 259209-17-1 ]
[ 1346607-49-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 80 °C 3: sodium / ethanol / 2 h / 90 °C 4: hydrogenchloride / 4 h / 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

11
[ 259209-17-1 ]
[ 1346607-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 18 h / 80 °C 3: sodium / ethanol / 8 h / 90 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

12
[ 259209-17-1 ]
[ 1346607-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

13
[ 259209-17-1 ]
[ 1346607-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / Reflux 2: toluene / 48 h / Reflux

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

14
[ 259209-17-1 ]
[ 1346607-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: xylene / 0.25 h / 140 °C / microwave irradiation

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

15
[ 259209-17-1 ]
[ 1346608-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 90 °C 2.2: 72 h / 50 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

16
[ 259209-17-1 ]
[ 1346608-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 18 h / 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

17
[ 259209-17-1 ]
[ 1346608-12-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / Reflux; Inert atmosphere 2: toluene / 18 h / 80 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1

18
[ 259209-17-1 ]
[ 1272673-95-6 ]
[ 1272674-58-4 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	Stage #1: [2-hydroxy-3-(methyloxy)phenyl]boronic acid; ethyl 3-amino-1-(4-bromophenyl)-1H-pyrrole-2-carboxylate hydrochloride With caesium carbonate In 1,4-dioxane; water for 1h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water	8 To a solution of ethyl 3-amino-1-(4-bromophenyl)-5-chloro-1 H-pyrrole-2-carboxylate hydrochloride (Intermediate 7; 14.85 g, 39.1 mmol) in 1.4-dioxane (412 mL) and water (50 mL) [2-hydroxy-3-(methyloxy)phenyl]boronic acid (9.87 g, 58.7 mmol), cesium carbonate (38.21 g, 1 17 mmol) under argon, was added palladium tetrakis (451 mg, 391 μη"οΙ).Τιβ reaction was heated at reflux for one hour.The reaction mixture was concentrated in vacuo, dissolved in DCM and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether/EtOAc 90/10, 80/20 and 70/30) to give the title compound, ethyl 3- amino-5-chloro-1-[2'-hydroxy-3'-(methyloxy)-4-biphenylyl]-1 H-pyrrole-2-carboxylate, (13.64 g, 90.3% yield) as a beige solid.1H NMR (DMSO d6, 400MHz): δ 8.76 (s, 1 H), 7.6 (d, 2H), 7.2 (d, 2H), 6.98 (d, 1 H), 6.9 (m, 2H), 5.88 (s, 1 H), 5.6 (brs, 2H), 3.9 (q, 2H), 3.86 (s, 3H), 0.91 (t, 3H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1 Location in patent: Page/Page column 40; 41

19
[ 259209-17-1 ]
[ 1272673-95-6 ]
[ 1346607-53-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: [2-hydroxy-3-(methyloxy)phenyl]boronic acid; ethyl 3-amino-1-(4-bromophenyl)-1H-pyrrole-2-carboxylate hydrochloride With caesium carbonate In 1,4-dioxane; water for 2h; Reflux; Stage #2: With hydrogenchloride In 1,4-dioxane; water	4 To a suspension of ethyl 3-amino-1 -(4-bromophenyl)-1 H-pyrrole-2-carboxylate hydrochloride (3.5 g, 1 1.32 mmol; Intermediate 3), in 1 ,4-dioxane (150 mL), water (150 mL) were added [2-hydroxy-3-(methyloxy)phenyl]boronic acid (1 1 .41 g, 67.9 mmol), palladium tetrakis (0.13 g, 0.1 1 mmol), cesium carbonate (12.91 g, 39.6 mmol). The reaction was stirred at reflux for 2 hours. After cooling, the mixture was filtered and treated with a 1 N HCI solution. The dioxane was evaporated and the compound was precipitated from the acid phase. The solid was filtered, washed with water and dried. The title compound ethyl 3-amino-1-[2'-hydroxy-3'-(methyloxy)-4- biphenylyl]-1 H-pyrrole-2-carboxylate hydrochloride was obtained (3.9 g, 1 1 .07 mmol, 98% yield) as a cream solid.LCMS: (M+H)+ = 353; Rt= 3.25 min.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/138307, 2011, A1 Location in patent: Page/Page column 39

20
[ 259209-17-1 ]
[ 1272674-01-7 ]
[ 1272674-58-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 90℃;

Reference： [1]Mirguet, Olivier; Sautet, Stephane; Clement, Catherine-Anne; Toum, Jeroime; Donche, Frederic; Marques, Celine; Rondet, Emilie; Pizzonero, Mathieu; Beaufils, Benjamin; Dudit, Yann; Huet, Pascal; Trottet, Lionel; Grondin, Pascal; Brusq, Jean-Marie; Boursier, Eric; Saintillan, Yannick; Nicodeme, Edwige [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 7, p. 632 - 636]

21
[ 259209-17-1 ]
[ 1272672-02-2 ]
[ 1272672-11-3 ]

Yield	Reaction Conditions	Operation in experiment
22.11%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In 1,4-dioxane; water at 160℃; for 0.25h; Microwave irradiation;

Reference： [1]Mirguet, Olivier; Sautet, Stephane; Clement, Catherine-Anne; Toum, Jeroime; Donche, Frederic; Marques, Celine; Rondet, Emilie; Pizzonero, Mathieu; Beaufils, Benjamin; Dudit, Yann; Huet, Pascal; Trottet, Lionel; Grondin, Pascal; Brusq, Jean-Marie; Boursier, Eric; Saintillan, Yannick; Nicodeme, Edwige [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 7, p. 632 - 636]

22
[ 259209-17-1 ]
[ 1174758-95-2 ]
[ 1445881-67-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) thiophene-2-carboxylate In 1,4-dioxane for 15h; Inert atmosphere; Reflux;

Reference： [1]Liu, Jingxin; Liu, Yingjie; Du, Wenting; Dong, Ying; Liu, Jun; Wang, Mang [Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7293 - 7297]

23
[ 259209-17-1 ]
[ 1432505-00-4 ]
[ 1445881-72-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) thiophene-2-carboxylate In 1,4-dioxane for 18h; Inert atmosphere; Reflux;

Reference： [1]Liu, Jingxin; Liu, Yingjie; Du, Wenting; Dong, Ying; Liu, Jun; Wang, Mang [Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7293 - 7297]

24
[ 259209-17-1 ]
[ 90-05-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	In dimethyl sulfoxide at 120℃; for 12h;

Reference： [1]Lee, Chun-Young; Ahn, Su-Jin; Cheon, Cheol-Hong [Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 12154 - 12160]

25
[ 259209-17-1 ]
[ 4408-64-4 ]
[ 1613586-39-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	In N,N-dimethyl-formamide at 120℃; for 3h; Inert atmosphere; Molecular sieve;

Reference： [1]Ahn, Su-Jin; Lee, Chun-Young; Cheon, Cheol-Hong [Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1767 - 1772]

26
[ 259209-17-1 ]
[ 33948-36-6 ]
2'-hydroxy-3'-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: [2-hydroxy-3-(methyloxy)phenyl]boronic acid; 2-iodocyclohex-2-en-1-one With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With sodium carbonate In 1,4-dioxane; water at 100℃; for 10h; Inert atmosphere;

Reference： [1]Li, Qilin; Zhang, Hongbin [Chemistry - A European Journal, 2015, vol. 21, # 46, p. 16379 - 16382]

27
[ 259209-17-1 ]
6-ethoxy-8-methoxy-2,3,5,6-tetrahydro-1H-naphtho[1,2-de]chromen-4(12aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.17 h / 20 °C / Inert atmosphere 1.2: 10 h / 100 °C / Inert atmosphere 2.1: bromine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 5.1: palladium dichloride; oxygen; copper dichloride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere; Reflux
	Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.17 h / 20 °C / Inert atmosphere 1.2: 10 h / 100 °C / Inert atmosphere 2.1: bromine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 5.1: bromine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere 5.2: 0 °C / Inert atmosphere 6.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 7.1: palladium dichloride; oxygen; copper dichloride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere; Reflux