[ CAS No. 182344-21-4 ] {[proInfo.proName]}

Name: 182344-21-4|(4-Hydroxy-3-methoxyphenyl)boronic acid|95%
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SKU: A183790
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Quality Control of [ 182344-21-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 182344-21-4 ]

SDS Specification

Alternatived Products of [ 182344-21-4 ]

Product Details of [ 182344-21-4 ]

CAS No. :	182344-21-4	MDL No. :	MFCD18397223
Formula :	C₇H₉BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UZFBWSFTHSYXCN-UHFFFAOYSA-N
M.W :	167.96	Pubchem ID :	11557349
Synonyms :

Calculated chemistry of [ 182344-21-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	44.78
TPSA :	69.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.44
Log Po/w (WLOGP) :	-0.92
Log Po/w (MLOGP) :	-0.59
Log Po/w (SILICOS-IT) :	-1.22
Consensus Log Po/w :	-0.46

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.4
Solubility :	6.74 mg/ml ; 0.0401 mol/l
Class :	Very soluble
Log S (Ali) :	-1.48
Solubility :	5.61 mg/ml ; 0.0334 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.83
Solubility :	24.6 mg/ml ; 0.147 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 182344-21-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 182344-21-4 ]

* 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.

Upstream synthesis route of [ 182344-21-4 ]
Downstream synthetic route of [ 182344-21-4 ]

[ 182344-21-4 ] Synthesis Path-Upstream 1~2

1
[ 864757-97-1 ]
[ 182344-21-4 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 44, p. 10559 - 10568

2
[ 7368-78-7 ]
[ 182344-21-4 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 44, p. 10559 - 10568

[ 182344-21-4 ] Synthesis Path-Downstream 1~42

1
[ 182344-21-4 ]
[ 809275-58-9 ]
N-ethyl-4-[(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-(4-hydroxy-3-methoxy-phenyl)-methyl]-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5493 - 5498

2
[ 864757-97-1 ]
[ 182344-21-4 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 10559 - 10568

3
[ 10343-15-4 ]
[ 182344-21-4 ]
[ 869728-94-9 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 10559 - 10568

4
[ 100007-87-2 ]
[ 182344-21-4 ]
3-(4'-hydroxy-3'-methoxy-biphenyl-4-yl)-1H-indeno[1,2-c]pyrazol-4-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7615 - 7618

5
[ 29540-83-8 ]
[ 182344-21-4 ]
[ 58005-51-9 ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 164 - 165

6
[ 916429-35-1 ]
[ 182344-21-4 ]
6-(4-hydroxy-3-methoxy-phenyl)-3-(5-piperidin-1-ylmethyl-1H-indol-2-yl)-1H-quinolin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5907 - 5912

7
[ 182344-21-4 ]
[ 882972-00-1 ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 164 - 165

8
[ 182344-21-4 ]
[ 882972-01-2 ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 164 - 165

9
[ 182344-21-4 ]
[ 882971-99-5 ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 164 - 165

10
[ 182344-21-4 ]
C₂₅H₂₀O [ No CAS ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 164 - 165

11
[ 182344-21-4 ]
[ 882972-02-3 ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 164 - 165

12
[ 7368-78-7 ]
[ 182344-21-4 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 10559 - 10568

13
[ 182344-21-4 ]
[ 113349-27-2 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 10559 - 10568

14
[ 846564-00-9 ]
[ 182344-21-4 ]
9-cyclopropyl-7-(4-hydroxy-3-methoxyphenyl)-8-methoxy-9H-isothiazolo[5,4-b]quinoline-3,4-dione hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Compound 18 is prepared by Suzuki Cross-Coupling Reaction of 17 and aryl boronic acid (R = H) or aryl boronic ester (R = alkyl). [0208] Under an atmosphere of argon, a reaction vessel is charged with 17 (0. 1 mmol), dimethylformamide (2 ML), tetrahydrofuran (2 mL), tetrakis (triphenylphosphine) palladium (0) (0. 01-0. 02 mmol), the desired boronic acid or ester (0. 3-0. 4 mmol), and a 1 M aqueous solution of sodium bicarbonate (1-2 mmol). The resulting mixture is irradiated with microwaves at 130 C for 10-20 min, allowed to cool, and evaporated to dryness under reduced pressure. The isolated residues are purified using preparative HPLC to give the desired products (95-99% purity). The purified products are isolated as TFA salts and converted to the corresponding hydrochloride salts by addition of a 5% aqueous solution of hydrochloric acid followed by evaporation ; this process is repeated twice.

Reference： [1]Patent: WO2005/19228,2005,A1 .Location in patent: Page/Page column 61-62

15
[ 1132610-04-8 ]
[ 182344-21-4 ]
[ 1132610-06-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 908 - 911

16
[ 185418-17-1 ]
[ 182344-21-4 ]
4'-hydroxy-3',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 864 - 869

17
[ 635682-35-8 ]
[ 182344-21-4 ]
4-(4'-hydroxy-3'-methoxyphenyl)-5,6,7-trimethoxycoumarin [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 864 - 869

18
6,7-dimethoxy-4-trifluoromethanesulfonyloxycoumarin [ No CAS ]
[ 182344-21-4 ]
[ 1214736-38-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 864 - 869

19
[ 100487-81-8 ]
[ 182344-21-4 ]
[ 1162190-57-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5065 - 5068

20
[ 1761-61-1 ]
[ 182344-21-4 ]
[ 1258636-92-8 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 8484 - 8488

21
[ 1285505-77-2 ]
[ 182344-21-4 ]
[ 1285504-43-9 ]

Yield	Reaction Conditions	Operation in experiment
24%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃;	Example 23Synthesis of N-[(E)-3-(4'-hydroxy-3'-methoxy-biphenyl-2-yl)-2-methyl-acryloyl]-guanidine<Step 1>Intermediate 1 (20 mg, 0.05 mmol) and <strong>[182344-21-4]3-methoxy-4-hydroxyphenyl boronic acid</strong> (10 mg, 0.06 mmol) were dissolved in a mixed solution of dioxane and water (v/v=3/1, 3 mL). Pd(PPh3)4 (3.00 mg, 2.60 mumol) and Na2CO3 (21.0 mg, 0.2 mmol) were added to the solution and then stirred at 90 C. overnight. After cooling it to room temperature, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1% TFA in water/CH3CN) to obtain the compound of Example 23 (5.2 mg, 24%).MS: 326

Reference： [1]Patent: US2011/82109,2011,A1 .Location in patent: Page/Page column 18-19

22
[ 1268826-55-6 ]
[ 182344-21-4 ]
[ 1340482-11-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7547 - 7557

23
[ 1419171-64-4 ]
[ 182344-21-4 ]
C₃₂H₂₈O₈S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 2h;Inert atmosphere;	Argon was flushed through a solution of intermediate D (130 mg, 0.236 mmol) and 4-hydroxy-3- methoxyphenylboronic acid (120 mg, 0.714 mmol) in a mixture of toluene (3 ml) and MeOH (3 ml). PEPPSI-iPr (26.1 mg, 0.036 mmol) and KF (125 mg, 2.14 mmol) were added and the reaction heated at 55 C for 120 min. The solvents were removed in vacuo and the crude was added water (3 ml), 5 M NaOH (1 ml) and dioxane (2 ml). The reaction was heated to 70C for 30 min then cooled, filtered and washed with water. 1 M NH4HCO3 was added and the product was collected as a solid by filtration. Water and 2 M HCl were added. The solid was once more collected by filtration and washed with water. Yield: 110 mg (77%) as a off white solid. 1H NMR (400 MHz, DMSO-i 6): delta 3.74 (s, 4H), 3.85 (s, 6H), 6.82 (d, J 8.3 Hz, 2H), 7.05 (dd, J8.28, 2.01 Hz, 2H), 7.17 (d, J2.0 Hz, 2H), 7.26 (s, 2H), 7.34 (s, 2H), 9.32 (s, 2H), 12.54 (br. s., 2H). HPLC: Rt = 2.61 mm, 99% (254 nm, 10-40% MeCN in 10 mM buffer, XBridge) and Rt = 2.60 mm, 98% (400 nm, 10-40% MeCN in 10 mM buffer, XBridge). LC-MS: m/z = 626 (M + 18).
	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 2h;Inert atmosphere;	Argon was flushed through a solution of intermediate D (130 mg, 0.236 mmol) and 4- hydroxy-3-methoxyphenylboronic acid (120 mg, 0.714 mmol) in a mixture of toluene (3 ml) and MeOH (3 ml). PEPPSI-iPr (26.1 mg, 0.036 mmol) and KF (125 mg, 2.14 mmol) were added and the reaction heated at 55 C for 120 min. The solvents were removed in vacuo and the crude was added water (3 ml), 5 M NaOH (1 ml) and dioxane (2 ml). The reaction was heated to 70C for 30 min then cooled, filtered and washed with water. 1 M NH4HCO3 was added and the product was collected as a solid by filtration. Water and 2 M HCl were added. The solid was once more collected by filtration and washed with water. Yield: 110 mg (77%) as a off white solid. 1H NMR (400 MHz, DMSO-i¾): delta 3.74 (s, 4H), 3.85 (s, 6H), 6.82 (d, J 8.3 Hz, 2H), 7.05 (dd, J8.28, 2.01 Hz, 2H), 7.17 (d, J2.0 Hz, 2H), 7.26 (s, 2H), 7.34 (s, 2H), 9.32 (s, 2H), 12.54 (br. s., 2H). HPLC: Rt = 2.61 min, 99% (254 nm, 10-40% MeCN in 10 mM buffer, XBridge) and Rt = 2.60 min, 98% (400 nm, 10-40% MeCN in 10 mM buffer, XBridge). LC-MS: m/z = 626 (M + 18).

Reference： [1]Patent: WO2013/9259,2013,A1 .Location in patent: Page/Page column 98; 99
[2]Patent: WO2013/36196,2013,A1 .Location in patent: Page/Page column 103

24
[ 1419171-68-8 ]
[ 182344-21-4 ]
[ 1419172-37-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 80℃; for 0.166667h;Inert atmosphere; Sealed tube;	Argon was bubbled through a mixture of intermediate N (60 mg, 0.10 mmol), 4-hydroxy-3 - methoxyphenylboronic acid (25 mg, 0.15 mmol) and KF (19 mg, 0.32 mmol) in MeOH/toluene (1 :1, 4 ml). After 10 min, PEPPSI-iPr (2 mg, 0.003 mmol) was added and the mixture stirred at 80 C in a sealed tube. After 10 min, the reaction was cooled to RT, diluted with CH2CI2 (30 ml), washed with water (30 ml) and the aqueous layer was subsequently extracted with DCM (15 ml x 2). The organic layers were combined and evaporated to dryness to obtain the crude product. The residue was purified by flash chromatography using toluene/EtOAc (6:1) as eluent. Yield: 55 mg (85%) The ester from above (55 mg, 0.08 mmol) was dissolved in dioxane (2 ml) and 2 M NaOH (2 ml) was added. After stirring 45 min at 70 C, the reaction was cooled to RT, diluted with water (11 ml) and acidified using 2 M HC1 (approx. 3 ml). The formed precipitate was isolated by centrifugation and washed two times with water. The material was dried under high vacuum for 48 hrs. Yield: 44 mg (86%); Red solid; 1H NMR (DMSO-i/6): delta 3.74 (s, 2H), 3.78 (s, 2H), 3.85 (s, 3H), 6.82 (d, J 8.0 Hz, IH), 7.06 (dd, J 8.0, 2.1 Hz, IH), 7.17 (d, J2.1 Hz, IH), 7.27 (d, J4.0 Hz, IH), 7.33 (d, J4.0 Hz, IH), 7.35 (s, IH), 7.40 (d, J4.0 Hz, IH), 7.47 (s, IH), 7.68 (d, J4.0 Hz, 1H), 9.33 (s, 1H), 12.74 (bs, 3H). HPLC: RT = 1.76 mm, 97% (254 nm, 10-40% MeCN in 10 mM buffer, 3 mm, XBridge) and RT = 1.77 mm, 97% (400 nm, 10-40% MeCN in 10 mM buffer, 3 mm, XBridge). LC-MS : m/z = 630 (M + NH^.
85%	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 80℃; for 0.333333h;Inert atmosphere;	Argon was bubbled through a mixture of intermediate N (60 mg, 0.10 mmol), 4-hydroxy-3- methoxyphenylboronic acid (25 mg, 0.15 mmol) and KF (19 mg, 0.32 mmol) inMeOH/toluene (1 : 1, 4 ml). After 10 min, PEPPSI-iPr (2 mg, 0.003 mmol) was added and the mixture stirred at 80 C in a sealed tube. After 10 min, the reaction was cooled to RT, diluted with CH2CI2 (30 ml), washed with water (30 ml) and the aqueous layer was subsequently extracted with DCM (15 ml x 2). The organic layers were combined and evaporated to dryness to obtain the crude product. The residue was purified by flash chromatography using toluene/EtOAc (6: 1) as eluent. Yield: 55 mg (85%)

Reference： [1]Patent: WO2013/9259,2013,A1 .Location in patent: Page/Page column 108; 109
[2]Patent: WO2013/36196,2013,A1 .Location in patent: Page/Page column 113

25
[ 1419171-84-8 ]
[ 182344-21-4 ]
[ 1419172-41-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 1.5h;Inert atmosphere;	Argon was bubbled through a mixture of <strong>[182344-21-4]4-hydroxy-3-methoxyphenylboronic acid</strong> (0.171 g, 1.02 mmol), KF (0.158 g, 3.00 mmol) and Intermediate E2 (0,159 g, 0,34 mmol) in MeOH/toluene (1 :1, 5 ml). After 15 min PEPPSI-iPr (12 mg, 0.017 mmol) was added and the mixture heated to 55 C. After 90 min, the reaction mixture was evaporated to dryness. The residue was purified by flash chromatography using toluene/EtOAc (6: 1?3 :1?1 :3?1 :6) as eluent. Yield: 101 mg (54%); 1H NMR (400 MHz, CDC13): delta 3.61 (s, 4H), 3.71 (s, 6H), 3.96 (s, 6H), 5.70 (bs, 2H), 6.94 (d, J 8.4 Hz, 2H), 7.07 (d, J 2.0 Hz, 2H), 7.13 (dd, J 8.4, 2.0 Hz, 2H), 7.18 (s, 2H). The ester from above (101 mg, 0.18 mmol) was dissolved in dioxane (3 ml), followed by addition of 2 M NaOH (3 ml) and water (1 ml). After stirring 45 min at 70 C, the reaction was cooled to RT, diluted with water (8 ml) and acidified using 1 M HC1 (approx. 6 ml). The formed precipitate was isolated by centrifugation and washed two times with water. The material was dried under high vacuum for 48 hrs. Yield: 82 mg (86%); brown solid. 1H NMR (DMSO-i/6): delta 3.48 (s, 4H), 3.84 (s, 6H), 6.82 (d, J 8.3 Hz, 2H), 7.01 (dd, J 8.3 , 2.0 Hz, 2H), 7.16 (d, J 2.0 Hz, 2H), 7.33 (s, 2H), 9.29 (s, 2H), 12.42 (bs, 2H). HPLC: RT = 1.91 mm. 96% at 254 nm (10-40% MeCN in buffer, 3 mm, XBndge) and RT = 1.91 mm, 100% at 400 nm (10-40% MeCN in buffer, 3 mm, XBndge). ). LC-MS: m/z = 544 (M + NH4+).
54%	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 1.75h;Inert atmosphere;	Argon was bubbled through a mixture of <strong>[182344-21-4]4-hydroxy-3-methoxyphenylboronic acid</strong> (0.171 g, 1.02 mmol), KF (0.158 g, 3.00 mmol) and Intermediate E2 (0, 159 g, 0,34 mmol) inMeOH/toluene (1 : 1, 5 ml). After 15 min PEPPSI-iPr (12 mg, 0.017 mmol) was added and the mixture heated to 55 C. After 90 min, the reaction mixture was evaporated to dryness. The residue was purified by flash chromatography using toluene/EtOAc(6: 1?3 : 1?1 :3?1 :6) as eluent. Yield: 101 mg (54%); 1H NMR (400 MHz, CDC13): delta 3.61 (s, 4H), 3.71 (s, 6H), 3.96 (s, 6H), 5.70 (bs, 2H), 6.94 (d, J 8.4 Hz, 2H), 7.07 (d, J2.0 Hz, 2H), 7.13 (dd, J 8.4, 2.0 Hz, 2H), 7.18 (s, 2H).

Reference： [1]Patent: WO2013/9259,2013,A1 .Location in patent: Page/Page column 112; 113
[2]Patent: WO2013/36196,2013,A1 .Location in patent: Page/Page column 117

26
[ 1419171-85-9 ]
[ 182344-21-4 ]
[ 1419172-36-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 1h;Inert atmosphere;	Argon was bubbled through a mixture of 4-hydroxy-3 -methoxyphenylboronic acid (0.186 g, 1.11 mmol), KF (0.172 g, 2.95 mmol) and intermediate F2 in MeOH/toluene (1 : 1, 8 ml). After 15 min PEPPSI-iPr (15 mg, 0.022 mmol) was added and the mixture heated to 55 C. After 60 min, the reaction mixture was evaporated to dryness, dissolved in CH2CI2 (30 ml) and washed with water (30 ml). The organic layer was evaporated to dryness to obtain the crude product. The residue was purified by flash chromatography using toluene/EtOAc (9:1?7:1) as eluent. Yield: 256 mg (80%); XH NMR (400 MHz, CDC13): delta 3.55 (s, 2H), 3.62 (s, 2H), 3.69 (s, 3H), 3.69 (s, 3H), 3.96 (s, 3H), 6.93 (d, J 8.0 Hz, 1H), 7.06 (d, J4 Hz, 1H), 7.10 (d, J 4.0 Hz, 1H), 7.12 (dd, J 4.0, 8.0 Hz, 1H), 7.17 (s, 1H), 7.39 (d, J 4.0 Hz, 1H). The ester from above (54 mg, 0.13 mmol) was dissolved in dioxane (2 ml) and 2 M NaOH (2 ml) was added. After stirring 45 min at 70 C, the reaction was cooled to RT, diluted with water (6 ml) and acidified using 2 M HC1 (approx. 3 ml). The formed precipitate was isolated by centrifugation and washed two times with water. The material was dried under high vacuum for 48 hrs. Yield: 26 mg (52%); White solid. 1H NMR (DMSO-i/6): delta 3.42 (s, 2H), 3.49 (s, 2H), 3.84 (s, 3H), 6.80 (d, J 8.2 Hz, IH), 7.01 (dd, J 8.2, 2.0 Hz, IH), 7.10 (d, J 5.3 Hz, IH), 7.15 (d, J2.0 Hz, IH), 7.32 (s, IH), 7.62 (d, J 5.2 Hz, IH), 9.28 (s, IH), 12.39 (bs, 2H). HPLC: RT = 1.20 mm, 99% (254 nm, 10-40% MeCN in 10 mM buffer, 3 mm, XBndge). LC-MS: m/z = 422 (M + NH^.
80%	With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 1.25h;Inert atmosphere;	Argon was bubbled through a mixture of <strong>[182344-21-4]4-hydroxy-3-methoxyphenylboronic acid</strong> (0.186 g, 1.11 mmol), KF (0.172 g, 2.95 mmol) and intermediate F2 in MeOH/toluene (1 : 1, 8 ml).After 15 min PEPPSI-iPr (15 mg, 0.022 mmol) was added and the mixture heated to 55 C. After 60 min, the reaction mixture was evaporated to dryness, dissolved in CH2CI2 (30 ml) and washed with water (30 ml). The organic layer was evaporated to dryness to obtain the crude product. The residue was purified by flash chromatography using toluene/EtOAc (9: 1?7: 1) as eluent. Yield: 256 mg (80%); 1H NMR (400 MHz, CDC13): delta 3.55 (s, 2H), 3.62 (s, 2H), 3.69 (s, 3H), 3.69 (s, 3H), 3.96 (s, 3H), 6.93 (d, J 8.0 Hz, 1H), 7.06 (d, J 4 Hz, 1H), 7.10 (d, J 4.0 Hz, 1H), 7.12 (dd, J4.0, 8.0 Hz, 1H), 7.17 (s, 1H), 7.39 (d, J 4.0 Hz, 1H).

Reference： [1]Patent: WO2013/9259,2013,A1 .Location in patent: Page/Page column 107; 108
[2]Patent: WO2013/36196,2013,A1 .Location in patent: Page/Page column 112

27
[ 1174429-23-2 ]
[ 182344-21-4 ]
[ 1174429-27-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1922 - 1939

28
[ 1469858-10-3 ]
[ 182344-21-4 ]
C₂₇H₃₀N₂O₃SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; toluene; at 100℃; for 8h;	A mixture of the corresponding intermediate 6-(4-Bromo-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.3 g, 0.9 mmol), 3,4-Dimethoxyphenylboronic acid (0.24 g, 1.5 mmol), Na2CO3 (2 M, 2.7 mL), and Pd(PPh3)2Cl2 (8 mg, 0.075 mmol) in toluene/ ethanol (1:1, 6 mL) was heated at 100 C. for 8 hr. The solution was cooled to room temperature and extracted with ethyl acetate. The target product was purified by gravity column chromatography (50% EtOAc in hexane) to give (3,4-Dimethoxy-phenyl)-{4-[4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl]-phenyl}-amine as brown solid in 42% yield.

Reference： [1]Patent: US2013/274255,2013,A1 .Location in patent: Paragraph 0187

29
2-amino-5-bromo-3-(3,4,5-trimethoxyphenyl)pyridine [ No CAS ]
[ 182344-21-4 ]
4-(6-amino-5-(3,4,5-trimethoxyphenyl)pyridin-3-yl)-2-methoxyphenol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7900 - 7915

30
[ 106-51-4 ]
[ 182344-21-4 ]
2,6-bis-(4-hydroxy-3-methoxyphenyl)-1,4-benzoquinone [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 13876 - 13879
Angew. Chem.,2014,vol. 126,p. 14096 - 14099,9

31
1-(2,3-dihydro-1H-inden-2-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
[ 182344-21-4 ]
4-[4-amino-1-(2,3-dihydro-1H-inden-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 2h;	To a solution of 1- (2,3-dihydro- 1 H-inden-2-yl)-3-iodo- 1 H-pyrazolo [3,4- d]pyrimidin-4-amine (300 mg, 0.795 mmol) in DMF (5 mL) was added 4-hydroxy-3- methoxyphenylboronic acid (200.4 mg, 1.19 mmol) at RT. Then, Na2CO3 (252.8 mg, 2.38 mmol) dissolved in water (5 mL) was added to the reaction mixture followed by addition of Pd(PPh3)4 (91.9 mg, 0.079 mmol) at RT and the resultant reaction mixture was heated at 100C for 2 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the reaction mixture was diluted with water (40 mL) and extracted with EtOAc (2x 100 mL). The combined organic layers were washed with water (2x50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude compound was purified by preparative HPLC to obtain 4- (4-amino-i- (2,3-dihydro- 1 H-inden-2-yl)- 1 Hpyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenol (44 mg) as an off-white solid. To this was added ethanolic HC1 (10 mL) and stuffed for 30 mm at RT. The reaction mixture was then concentrated under reduced pressure and lyophilized to afford 4- (4-amino- i-(2,3-dihydro- 1H-inden-2-yl)- 1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenol (45 mg) as the HC1 salt (off-white solid). ?HNMR (400 MHz, Methanol-d4) oe (ppm): 8.41 (s, 1H), 7.30 -7.16 (m, 5H), 7.19-7.08 (m, 1H), 6.98 (d, I = 8.1 Hz,1H), 5.86 (t, I = 8.1 Hz, 1H), 3.91 (s, 3H), 3.63 (dd, I = 15.9, 7.8 Hz, 2H), 3.57 - 3.46 (m, 2H).

Reference： [1]Patent: WO2015/58084,2015,A1 .Location in patent: Paragraph 0370

32
[ 1394431-52-7 ]
[ 182344-21-4 ]
[ 1394431-67-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4403 - 4407

33
C₁₆H₁₃ClFN₃O₂ [ No CAS ]
[ 182344-21-4 ]
C₂₃H₂₀FN₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 100℃; for 10h;	General procedure: SI-6 (100 mg, 0.321 mmol), <strong>[182344-21-4]4-hydroxy-3-methoxyphenylboronic acid</strong> (65 mg, 0.39 mmol) , K3PO4 (204 mg, 0.962 mmol), and PdCl2(PPh3)2 (11 mg, 0.02 mmol) were taken in DMF (2.0 mL) and water (0.25 mL). The mixture was heated at 100 C for 10 hr, cooled, concentrated, diluted with DCM, and filtered through a PL-Thiol MP Resin cartridge (Agilent). The filtrate was concentrated and purified by flash SiO2 chromatography (0 to 25% MeOH/DCM) to obtain pure 32 (75 mg, 0.19 mmol, 59%).