[ CAS No. 108238-09-1 ] {[proInfo.proName]}

Name: 108238-09-1|2-Phenoxybenzeneboronic acid|98%
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Quality Control of [ 108238-09-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 108238-09-1 ]

SDS Specification

Alternatived Products of [ 108238-09-1 ]

Product Details of [ 108238-09-1 ]

CAS No. :	108238-09-1	MDL No. :	MFCD01001592
Formula :	C₁₂H₁₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AVOWPOFIQZSVGV-UHFFFAOYSA-N
M.W :	214.03	Pubchem ID :	2773559
Synonyms :

Calculated chemistry of [ 108238-09-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	62.78
TPSA :	49.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.35
Log Po/w (WLOGP) :	1.16
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	0.42
Consensus Log Po/w :	1.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.212 mg/ml ; 0.00099 mol/l
Class :	Soluble
Log S (Ali) :	-3.03
Solubility :	0.198 mg/ml ; 0.000926 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.55
Solubility :	0.0599 mg/ml ; 0.00028 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.53

Safety of [ 108238-09-1 ]

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 [ 108238-09-1 ]

* 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.

Upstream synthesis route of [ 108238-09-1 ]
Downstream synthetic route of [ 108238-09-1 ]

[ 108238-09-1 ] Synthesis Path-Upstream 1~8

1
[ 5419-55-6 ]
[ 7025-06-1 ]
[ 108238-09-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 3 h; Inert atmosphere Stage #2: at -78℃; for 2 h; Inert atmosphere	The 1-bromo-2-phenoxybenzene 0.018 µM is dissolved in 100 ml, in dry THF, added after the never-dried 500 ml three-mouth bottle, N₂-78 °C under the protection of the reaction 30min, slow adds by drops positively BuLi 0.027 µM, after dropping maintain -78 °C reaction 3h, then slowly dropping triisopropyl borate 0.02 µM, after dropping the reaction is maintained in the -78 °C reaction 2h, slow heating to room temperature, the reaction overnight, TLC monitoring after the reaction is completed, water slow quenching the reaction solution, extraction to dryness, to obtain 2-phenoxyphenylboronic acid (B-1) 0.0144 µM, and the yield is 80percent. Mass spectrum: 214.06.

Reference： [1] Patent: CN106565434, 2017, A, . Location in patent: Paragraph 0128-0131

2
[ 101-84-8 ]
[ 108238-09-1 ]

Reference： [1] Patent: EP1444981, 2004, A1, . Location in patent: Page/Page column 61

3
[ 7732-18-5 ]
[ 108238-09-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 23, p. 6420 - 6423

4
[ 121-43-7 ]
[ 34883-46-0 ]
[ 108238-09-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 38, p. 12313 - 12317[2] Angew. Chem., 2018, vol. 130, # 38, p. 12493 - 12497,5

5
[ 13675-18-8 ]
[ 2688-84-8 ]
[ 108238-09-1 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580

6
[ 101-84-8 ]
[ 121-43-7 ]
[ 108238-09-1 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1993, vol. 66, # 11, p. 3483 - 3491

7
[ 1431616-58-8 ]
[ 108238-09-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 23, p. 6420 - 6423

8
[ 1008106-86-2 ]
[ 108238-09-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 23, p. 6420 - 6423

[ 108238-09-1 ] Synthesis Path-Downstream 1~88

1
[ 952591-27-4 ]
[ 108238-09-1 ]
[ 952591-43-4 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3733 - 3736

2
[ 108238-09-1 ]
[5-(2-phenoxyphenyl)furan-2-ylcarbonyl]guanidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2882 - 2891

3
[ 24250-84-8 ]
[ 108238-09-1 ]
[ 660830-58-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 75℃; for 12h;	The title compound was prepared following the procedure D using (L)-4- [BROMOPHENYLALANINE] (8.55g, 35.0 mmol), <strong>[108238-09-1]2-phenoxyphenyl boronic acid</strong> (10. [00G,] 46.73 [MMOL),] and palladium tetrakis-triphenylphosphine (4.0 g, 10% [MMOL))] and 2N [NA2CO3] aq. solution (70 mL, 140 [MMOL)] in 140 ml of DME. After removal of solvents, the solid was washed with ether to afford the title compound as the HCI salt (10.0 g, 26.20 mmol, 75% yield).

Reference： [1]Patent: WO2004/14844,2004,A2 .Location in patent: Page 179; 181-182

4
[ 815580-04-2 ]
[ 108238-09-1 ]
6-(2-phenoxyphenyl)-4H-spiro[1,3-benzodioxine-2,4'-piperidine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.5%	With sodium hydrogencarbonate; triphenylphosphine;palladium diacetate; In ethanol; water; for 18h;Heating / reflux;	To a solution 'of 6-bromo-4H-spiro[1,3-benzodioxine-2,4'-piperidine] (l.OOg, 3.5mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.90g, 4.2mmol), triphenyl phosphine (0.13g, 0.52mmol) and sodium hydrogencarbonate (l.OSg, lOmmol) in ethanol/water (4:1) (80ml) was added palladium (II) acetate (0.22g, Immol) . The mixtur.e was heated at reflux under a nitrogen atmosphere for 18hrs. The mixture was evaporated in vacuo and the residue suspended in dichloromethane (80ml) filtered and the filtrate washed with 2M sodium hydrogencarbonate solution (60ml) and brine (60ml). The organic layer was dried with magnesium sulfate and the solvent removed in vacuo and the crude material purified by column chromatography using a mixture of dichloromethane and methanol to give (0.48g, 36.5%) of the title compound as an orange gum; HPLC (99.24%; RT 2.40min); ^ NMR (CDC13) : 5= 1.85-2.01 (m, 4H, 2xCH2) , 2.98-3.02 (m, 4H, 2xCH2) , 3.39 (br s, 1H, NH) , 4.82 (s, 2H, -CH2O), 6.82-7.38 (m, 12H, ArH) ; 13C NMR (CDC13) : 8= 34.0, 42.6, 60.17, 67.06, 97.87, 116.8, 118.0, 199.1, 120.1, 122.6, 124.0, 125.4, 128.3, 129.1, 129.5, 130.1, 130.9, 133.0, 149.9, 153.4, 157.7; MS (electrospray; [M + H]+) m/z: 374.

Reference： [1]Patent: WO2004/111056,2004,A2 .Location in patent: Page 43-44

5
[ 108238-09-1 ]
[ 183208-35-7 ]
5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; for 4h;	To a solution of the 5-bromoazaindole 24 (15.0 g, 76.1 mmol) in toluene (360 mL) and EtOH (360 mL) was added LiCl (9.68 g, 228. 4 mmol), dichlorobis (triphenylphosphine) palladium (II) (5.34 g, 7.6 MMOL), 2- PHENOXYPHENYLBORONIC acid (24. 44 g, 114.2 mmol) and 1 M sodium carbonate (190 mL, 190 mmol). After 4 h, the mixture was allowed to cool to room temperature and the phases separated. The aqueous layer was washed with EtOAc (3x) and the combined organic extracts dried (MGS04), filtered and evaporated. The resulting residue was purified by silicagel chromatography [gradient elution, hexanes to HEXANES-ETOAC (1: 1)] to afford product 25 (18. 30 g, 84%) AS A CREAM-COLOURED SOLID. 1H NMR (400 MHZ, CDCL3) No. 6. 51 (DD, J = 3.5, 2. 0HZ, LH), 6.92-6. 96 (M, 2H), 7. 01 (t, J = 7.4 Hz, 1H), 7.05 (dd, J = 8. 1, 1.2 Hz, 1H), 7.22-7. 28 (M, 3H), 7.30-7. 34 (m, 2H), 7.52 (dd, J = 7. 5, 1.8 Hz, 1H), 8.13 (d, J = 2.0 Hz, 1H), 8. 52 (d, J = 2.0 Hz, 1H), 9. 82 (bs, 1H).

Reference： [1]Patent: WO2004/78756,2004,A2 .Location in patent: Page 113-114

6
5-bromo-3-oxazol-5-yl-pyrrolo [2,3-b]pyridine [ No CAS ]
[ 108238-09-1 ]
3-oxazol-5-yl-5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene;Heating / reflux;	A mixture of bromide 22 (300 mg, 1.14 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (366 mg, 1.71 mmol), PdCl2 (PPh3) 2 (80. 0 mg, 0.114 mmol), LiCl (145 mg, 3.42 mmol) and 1M NA2C03 (2.85 mL, 2.82 mmol) in toluene (5.4 mL) and EtOH (5.4 mL) was refluxed overnight (105 C oil bath temp. ). The reaction mixture was cooled, and separated between brine (20 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (2 x 30 mL). The combined organic solutions were dried (MGS04) and concentrated. The resulting solid was dry loaded on a silicagel column. Fractions containing the product were eluted using ethyl acetate: hexane (1: 1) (gradient elution) to give a solid which was triturated with ether to give 23 as a white solid (186 mg, 46%); H NMR (400 MHz, CDCl3) 8 6.94 (dd, J = 8. 8,1. 0 Hz, 2H), 7.05 (t, J = 7.4 Hz, 1H), 7.08 (s, 1H), 7.12 (dd, J = 8. 1,1. 1 HZ, 1H), 7.33-7. 20 (m, 3H), 7.38 (dt, J = 9. 2,1. 7 HZ, 1H), 7.56 (dd, J = 7. 6, 1. 8 Hz, 1H), 7.64 (d, J = 2. 4 Hz, 1H), 7.85 (s, 1H), 8. 32 (d, J = 2.0 Hz, 1H), 8.59 (d, J = 2.0 Hz, 1H), 9.35-9. 20 (bs, NH).

Reference： [1]Patent: WO2004/78756,2004,A2 .Location in patent: Page 110; 112

7
[ 24250-84-8 ]
[ 108238-09-1 ]
[ 845529-99-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 10 (2S)- [5-CHLORO-2- (5-DIMETHYLAMINO-NAPHTHALENE-L-SULFONYLAMINO)-BENZOYLAMINO]-3- (2 - phenoxy-biphenyl-4-yl)-propionic acid (2S)-AMINO-3- (2 -PHENOXY-BIPHENYL-4-YL) propionic acid methyl ester was prepared by following Procedure D using (S)-4-BROMO-PHENYL alanine (7. 32 g, 30 MMOL), 2-phenoxy- benzene boronic acid (12.84 g, 60 mmol), palladium tetrakis-triphenylphosphine (3.47 g, 3 mmol) and NA2C03 (AQ) (2.0 N, 75 mL, 150 mmol) in DME (180 mL). The mixture was heated at 90 C for 16 h. After completion of the reaction, 4 N HC1 in dioxane solution was added to neutralize the reaction mixture. The solvents were evaporated. The solid residue was washed with ether to remove some impurities, and then refluxed with 4 N HC1 in dioxane solution (15 mL) and methanol (120 mL) for 6 h to form methyl ester-hydrochloride salt.

Reference： [1]Patent: WO2005/14532,2005,A1 .Location in patent: Page/Page column 57

8
[ 108238-09-1 ]
[ 209808-18-4 ]
C₃₄H₄₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 0.666667h;Microwave irradiation;	To a mixture of INTERMEDIATE 5 (0.200 g, 0.443 MMOL), (2- phenoxyphenyl) boronic acid (0.142 g, 0.664 MMOL), toluene (3.6 mL), ethanol (0.84 mL), and 2.0 M NA2CO3 (0.56 mL) in a N2 purged microwave process vial was added palladium tetrakistriphenylphosphine (0.0511 g, 0.044 MMOL). The resulting mixture was subjected to microwave irradiation and heated to 120 C FOR 40 min. The reaction was then CONCENTRATED IN VACUO and the residue was diluted with water (4 mL) and CH2CI2 (4 mL). The layers were separated, and the aqueous phase was extracted with CH2CI2. The combined organic phases were dried over NA2S04, filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with 2: 1 toluene : EtOAc. The purified product was dissolved in CH2CI2 (10 mL) and trifluoroacetic acid (I mL) was added. After 2 h, the reaction was concentrated in vacuo. The residue was LYOPHILIZED from CH3CN/H20 to give COMPOUND 1 as its trifluoroacetic acid salt (0.196 g, 68%) as a slightly yellow solid. Purity (HPLC): > 99% ; 1H NMR (400MHZ, CD30D) 6 1. 08 (br t, J = 6.7 Hz, 3H), 1.22 (br t, J = 6.8 Hz, 3H), 2.41-2. 66 (m, 4H), 2.96-3. 13 (m, 2H), 3.14-3. 27 (m, 4H), 3.45-3. 58 (m, 2H), 6.71-6. 77 (m, 2H), 6.90 (dd, J ZIZI Hz, 8.1 Hz, 1H), 7.00- 7.06 (m, 1H), 7.16-7. 36 (m, 9H). Found: C, 61.32 ; H, 5.41 ; N, 4.45. C29H32N202 X 1.7 CF3CO2H has C, 61.34 ; H, 5.35 ; N, 4.42 %.
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 120℃; for 0.666667h;	To a mixture of INTERMEDIATE 5 (0.200 g, 0.443 mmol), (2- phenoxyphenyl) boronic acid (0. 142 g, 0.664 MMOL), toluene (3.6 mL), ethanol (0.84 mL), and 2.0 M NA2CO3 (0.56 mL) in a N2 purged microwave process vial was added palladium tetrakistriphenylphosphine (0. 0511 g, 0.044 MMOL). The resulting mixture was subjected to microwave irradiation and heated to 120 C for 40 min. The reaction was then concentrated in vacuo and the residue was diluted with water (4 mL) and CH2CI2 (4 mL). The layers were separated, and the aqueous phase was extracted with CH2CI2. The combined organic phases were dried over NA2SO4, filtered, and CONCENTRATED IN VACUO. The crude product was purified by silica gel column chromatography eluting with 2: 1 toluene : EtOAc. The purified product was dissolved in CH2C12 (10 mL) and trifluoroacetic acid (1 mL) was added. After 2 h, the reaction was concentrated in vacuo. The residue was LYOPHILIZED from CH3CN/H20 to give COMPOUND 1 as its trifluoroacetic acid salt (0.196 g, 68%) as a slightly yellow solid. Purity (HPLC): > 99% ; 1H NMR (400MHZ, CD30D) 5 1.08 (br t, J = 6.7 Hz, 3H), 1.22 (br t, J = 6.8 Hz, 3H), 2.41-2. 66 (m, 4H), 2.96-3. 13 (m, 2H), 3.14-3. 27 (m, 4H), 3.45-3. 58 (m, 2H), 6. 71-6. 77 (m, 2H), 6.90 (dd, J = 1.1 Hz, 8.1 Hz, IH), 7.00- 7.06 (m, 1H), 7.16-7. 36 (m, 9H). Found: C, 61.32 ; H, 5.41 ; N, 4.45. C29H32N202 X 1.7 CF3CO2H has C, 61.34 ; H, 5.35 ; N, 4.42 %.

Reference： [1]Patent: WO2004/101519,2004,A1 .Location in patent: Page 20; 36-37
[2]Patent: WO2004/100952,2004,A1 .Location in patent: Page 36-37

9
[ 757978-34-0 ]
[ 108238-09-1 ]
5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; toluene; at 105℃;	A mixture of 8 (40.0 mg, 0.11 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (35.5 mg, 0.166 mmol), PDCL2 (PPH3) 2 (7.8 mg, 0.011 MMOL), LiCl (14.0 mg, 0.33 mmol), 1M NA2CO3 (276 muL, 0.28 mmol) in EtOH (0.66 mL) and toluene (0.66 mL) was heated at 105 C for 0.5 h in a sealed reaction tube. Reaction mixture was separated between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (2x). The combined organic solutions were concentrated and purified by PTLC using ethyl acetate: hexane (1: 1) as eluent to give 9 as a white solid (13.8 mg, 40%) ; 1H NMR (400 MHz, CDCl3) 8 12.80-12. 60 (bs, NH), 8.69 (d, J = 2.0 Hz, 1H), 8.34 (d, J = 2.0 Hz, 1H), 7.87 (s, 1H), 7. 53 (dd, J = 7.6, 1.7 Hz, 1H), 7.40 (dt, J = 7.5, 1.8 Hz, 1H), 7.29 (M, 3H), 7.06 (M, 2H), 6.94 (M, 2H); MS (CI) m/z 352.8 (MH+MeCN).

Reference： [1]Patent: WO2004/101565,2004,A2 .Location in patent: Page 45

10
[ 101-84-8 ]
[ 108238-09-1 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 3 2-phenoxyphenylboronic acid diphenyl ether (0.85g) was dissolved in anhydrous tetrahydrofuran (20ml) and the reaction mixture was cooled to 0C. N-butyllithium (1.6M, 3.1ml) was delivered by drops thereto and the reaction mixture was stirred for 30 minutes at the same temperature.. trimethyl borate (0.68ml) was added thereto and the reaction mixture was stirred for two hours at room temperature. 1N hydrochloric acid was added to the reaction mixture and the water layer was extracted with ethyl acetate.. The organic layer was dried with anhydrous sodium sulfate.. The solvent was distilled off and the obtained residue was purified by column chromatography (ethyl acetate: hexane = 1.5:1 to 1:3) to obtain the title compound (304mg) having the following physical data. TLC: Rf 0.57 (ethyl acetate: hexane = 1:3)

Reference： [1]Patent: EP1444981,2004,A1 .Location in patent: Page/Page column 61

11
[ 108238-09-1 ]
[ 111-42-2 ]
[ 515158-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃; for 1h;	Reference Example 4 6-methyl-2-(2-phenoxyphenyl)-1,3,6,2-dioxy azaborocane The compound produced in Reference Example 3 (304mg) was dissolved in ethanol (10ml) and diethanolamine (169mg) was added thereto and the mixture was stirred for one hour at room temperature.. The solvent was distilled off to obtain the title compound (403mg) having the following physical data. NMR (CDCl3): delta 7.76 (1H, dd, J=7, 3 Hz), 6.7-7.3 (8H, m), 4.01 (2H, t, J=7 Hz), 3.92 (2H, t, J =7 Hz), 3.13 (4H, t, J=7 Hz), 2.64 (3H, s).

Reference： [1]Patent: EP1444981,2004,A1 .Location in patent: Page/Page column 62

12
5-hydroxy-2-propionylamino-benzoic acid methyl ester [ No CAS ]
[ 108238-09-1 ]
C₂₃H₂₁NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; copper diacetate; In dichloromethane; at 20℃; for 72h;Molecular sieve;	EXAMPLE 6; 5- (2-Phenoxy-phenoxy)-2-propionylamino-benzoic acid; A mixture of 5-hydroxy-2-propionylamino-benzoic acid methyl ester (2.2 g, 10 mmol), (2- phenoxy) phenylboronic acid (4.3 g, 20 mmol), anhydrous copper (In acetate (1.8 g, 10 mmol) and pyridine (4.0 g, 50 mmol) in CH2C12 (50 mL) was stirred at room temperature for 72 h in the presence of 5 A powdered molecular sieves. The reaction mixture was then filtered through Celite and chromatographed on silica gel (Rf = 0. 11, CH2C12) to give the intermediate methyl ester. This was dissolved in a mixture of methanol (5 mL) and 1M NaOH (5 mL), warmed at 60 C for 1 h, and then acidified to pH 3 with 1 M HCl. After cooling, the pure title compound wa"s"*coflected by filtration, dried, and obtained as a grey solid (0.34 g,'9R% yield). 'H NMR (CDC13) 8 1.27 (t, 3H), 2.48 (q, 2H), 6.90 (d, 2 H), 7.03-7. 10 (m, 3H), 7.11-7. 19 (m, 3H), 7.28 (t, 2H), 7.64 (d, 1H) 8.69 (d, 1H), 10.7 (bs, 1H). In essentially the same manner the following compounds were obtained from the correspond- ing starting materials: 2-Propionylamino-5-(3-trifluoromethyl-phenoxy)-benzoic acid 'H NMR (CD30D) 8 1.25 (t, 3H), 2.48 (q, 2H), 7.22 (d, 1 H), 7.26 (s, 1H), 7.30 (dd, 1H), 7.42 (d, 1H), 7.56 (t, 1H), 7.72 (d, 1H), 8.63 (d, 1H)

Reference： [1]Patent: WO2005/75410,2005,A1 .Location in patent: Page/Page column 21

13
[ 880778-91-6 ]
[ 108238-09-1 ]
[ 880778-93-8 ]

Yield	Reaction Conditions	Operation in experiment
8%	With potassium hydroxide;bis(dicyclohexylamine)-palladium(II) acetate; In ethanol; N,N-dimethyl-formamide; at 100℃;	B. PREPARATION OF 1.4-DIMETHYL-5- (2-PHENOXY-PHENYL)--. H- PYRROLE-3-CARBOXYLIC ACID (4-METHANESULFONYL-PHENYL)-AMIDE; [00969] Into a 5OmL round bottom flask was weighed 100 mg of 2-Bromo-1 , 3- dimethyl-1H-pyrrole-4-carboxylic acid [4-(sulfamoyl)phenyl]-amide.(0.27mmol), 230mg of <strong>[108238-09-1](2-phenoxy)phenylboronic acid</strong>, potassium hydroxide(30.2 mg, 0.54 mmol), and DAPCy (J.Org Chem 2004, 69, 4330-4335) (6.2 mg, 4 Mol%) and Ethanol/ DMF (3 ml, 50:50) was added. The solution was heated at 1000C overnight. The reaction was cooled and washed into a separatory funnel with ethyl acetate and water. The ethyl acetate washed with water and brine, then was dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2), eluting with EtOAc/ Hex 0-80% to afford the title compounds as a white solid (10mg, 8%); 1H NMR (DMSO-c/6): delta 7.88(d, J = 9 Hz, 2H), 7.77(d, J = 9 Hz, 2H), 7.60(s, 1 H), 7.43-7.37(m, 1 H), 7.32-7.20(m, 4H), 7.04(d, J = 9 Hz, 2H), 6.85(d, J = 8 Hz, 2H), 3.52(s, 3H), 3.04(s, 3H), 2.20(s, 3H); MS (ESI) m/z 461 [M+H]+
8%	With potassium hydroxide;DAPCy; In ethanol; N,N-dimethyl-formamide; at 100℃;	B. Preparation of 1,4-dimethyl-5-(2-phenoxy-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide Into a 50 mL round bottom flask was weighed 100 mg of 2-Bromo-1,3-dimethyl-1H-pyrrole-4-carboxylic acid [4-(sulfamoyl)phenyl]-amide (0.27 mmol), 230 mg of <strong>[108238-09-1](2-phenoxy)phenylboronic acid</strong>, potassium hydroxide (30.2 mg, 0.54 mmol), and DAPCy (J. Org Chem (2004), 69: 4330-4335) (6.2 mg, 4 Mol %) and Ethanol/DMF (3 ml, 50:50) was added. The solution was heated at 100 C. overnight. The reaction was cooled and washed into a separatory funnel with ethyl acetate and water. The ethyl acetate washed with water and brine, then was dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2), eluting with EtOAc/Hex 0-80% to afford the title compounds as a white solid (10 mg, 8%); 1H NMR (DMSO-d6): delta 7.88 (d, J=9 Hz, 2H), 7.77 (d, J=9 Hz, 2H), 7.60 (s, 1H), 7.43-7.37 (m, 1H), 7.32-7.20 (m, 4H), 7.04 (d, J=9 Hz, 2H), 6.85 (d, J=8 Hz, 2H), 3.52 (s, 3H), 3.04 (s, 3H), 2.20 (s, 3H); MS (ESI) m/z 461 [M+H]+

Reference： [1]Patent: WO2006/76202,2006,A1 .Location in patent: Page/Page column 132
[2]Patent: US2008/234270,2008,A1 .Location in patent: Page/Page column 68

14
[ 919118-89-1 ]
[ 108238-09-1 ]
1-[4-(2'-phenoxybiphenyl-2-ylamino)piperidin-1-yl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 150℃; for 0.25h;Microwave irradiation;	l-[4-(2'-Phenoxybiphenyl-2-ylamino)piperdin-l-yI]ethanone hydrochlorideSTX2048C25H26N2O2, MW: 386.49 EPO <DP n="210"/>To a solution of l-(4-(2-bromophenylamino)piperidin-l-yl)ethanone (97 mg, WBHOl 149, 0.33 mmol), <strong>[108238-09-1]2-phenoxyphenyl boronic acid</strong> (105 mg, 0.49 mmol) and sodium carbonate (70 mg, 0.66 mmol) in a mixture of 1:1 toluenerwater (4 ml) was added Pd(PPli3)4 (19 mg, 0.017 mmol). This mixture was then heated in a CEM discover microwave instrument at 15O0C for 10 min. Analysis by TLC indicated that the reaction hadn't reached completion, therefore, further Pd(PPlIs)4 (19 mg, 0.017 mmol) was added. This mixture was again heated in the CEM MW at 15O0C for 5 min. This mixture was then diluted with water (10 ml) and extracted with EtOAc (3 x 10 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography then proceeded (eluant; HexrEtOAc 1:1) and the relevant fractions were evaporated in vacuo to afford the desired product as a transparent oil (41.4 mg, 33%). As a further and necessary purification step, ethereal HCl (0.23 ml, 2M in ether, 0.45 mmol) was slowly added to a stirred solution of the product in ether. This provided a white precipitate, which was then centrifuged for 10 min. The mother liquor was decanted and the obtained white solid was washed with cold ether (3 x 2 ml). The white solid was dried under nitrogen to afford the title compound as the desired product (11.8 mg, 9%).LCMS: M+H: 387.65 (1.38 min, 95% MeOH and 5% Water at 1.0 ml/min). HPLC: 84.14% purity (4.92 min, isocratic 70% MeOH, 30% water at 0.5 ml/min

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 207-208

15
[ 890051-43-1 ]
[ 108238-09-1 ]
3-(2'-phenoxy-biphenyl-4-yloxymethyl)-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 15 3-(2'-Phenoxy-biphenyl-4-yloxymethyl)-benzoic acid A degassed solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of Inter-mediate 1; 74 mg, 0.2 mmol) in dioxane (4 mL) and a degassed solution of potassium carbonate (83 mg) in water (0.4 mL) were added to a reaction vial containing <strong>[108238-09-1](2-phenoxy)phenylboronic acid</strong> (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.; 128 mg, 0.6 mmol). The solution was degassed and bis(tri-cyclohexylphos-phine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 7 mg, 0.01 mmol) was added. The mixture was heated in a microwave oven at 170 degrees for 25 min. The reaction mixture was filtered through silica, and washed with dioxane (1 mL) and dimethylacetamide (1 mL). 2 M potassium hydroxide solution (0.4 mL) was added. The mixture was stirred at room temperature overnight, and then 1 M HCl (0.8 mL) was added. The solvent was evaporated and the residue was triurated with 50% aqueous methanol to give 3-(2'-phenoxy-biphenyl-4-yloxymethyl)-benzoic acid. Mass spectrum MH+=397.

Reference： [1]Patent: US2006/122256,2006,A1 .Location in patent: Page/Page column 30

16
[ 942154-19-0 ]
[ 108238-09-1 ]
1-(2'-phenoxybiphenyl-3-ylmethyl)-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrabutylammomium bromide; potassium carbonate;palladium diacetate; In ethanol; water; at 120℃; for 0.05h;Irradiation;	l-(2'-Phenoxy-biphe?yl-3-yImethyI)-lH-[l,2,4]triazole (TJA01135, STX1835) C21H17N3O MW 327.38. A 10 mL microwave vial was loaded with TJA01009 (0.100 g, 0.420 mmol), 4- phenoxyphenylboronic acid (0.135 g, 0.630 mmol), potassium carbonate (0.145 g, 1.05 mmol), tetrabutylammonium bromide (0.139 g, 0.420 mmol), Pd(OAc)2 (0.002-0.003 g, 2-3 mol %), ethanol (1.5 mL) and distilled water (3.5 mL). The vial was sealed and loaded (with no prior degassing) into a CEM Discover Microwave. After a run time of 3 min at 120 0C the reaction mixture was allowed to cool and ethyl acetate (50 mL) added. This was then washed with distilled water (30 mL x 3) and brine (30 mL). The organic layer was dried over MgSO4, filtered and solvent removed in vacuo to leave a yellow/brown residue. The crude product was purified by flash chromatography (20 g column, method4) eluting the title compound as a light yellow viscous oil (0.120 g, 88 %), R/. 0.44 (ethyl acetate); 1H NMR (270 MHz, DMSO-^6) delta 5.41 (2H, s, ArCH2N), 6.83-6.86 (2H, d, J= 1.1 Hz, ArH), 6.98-7.05 (2H, m, ArH), 7.19-7.51 (HH, m, ArH), 7.97 (IH, s, C2H2N3) and 8.63 (IH, s, C2H2N3);13C NMR (67.9 MHz, CDCl3) delta 53.7, 117.9, 120.1, 120.4, 122.8, 124.3, 126.9, 129.0, 129.2, 129.6, 129.7, 131.2, 132.9, 134.4, 138.7, 143.1, 152.2, 153.5 and 157.7; HPLC (90 % CH3CN in H2O) rr= 2.278 (98.66 %); LCMS (APCI), m/z 328.46 (M+ + H, 100%);

Reference： [1]Patent: WO2007/68905,2007,A1 .Location in patent: Page/Page column 109-110

17
N-(6-(6-amino-5-chloropyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide [ No CAS ]
[ 108238-09-1 ]
N-(6-(6-amino-5-(2-phenoxyphenyl)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 125℃; for 0.25h;Microwave irradiation;Product distribution / selectivity;	Example 17; Preparation of lambda/-(6-(6-amino-5-(2-phenoxyphenyl)pyridin-3-yl)imidazo[l,2-b]pyridazin-2- yl)acetamideA mixture of lambda/-(6-(6-amino-5-chloropyridin-3-yl)imidazo[ 1 ,2-b]pyridazin-2- yl)acetamide (15 mg, 0.05 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (32 mg, 0.15 mmol) and l,l-bis(diphenylphosphino)ferrocene palladium (II) chloride-dichloromethane complex (40 mg, 0.05 mmol) in 0.5 mL solution of DME and 2 M aq. sodium carbonate (3:1) was heated in the microwave at 125C for 900 seconds. The crude product was purified by reverse phase prep HPLC to give 7V-(6-(6-amino-5-(2-phenoxyphenyl)pyridin-3-yl)imidazo[l,2- b]pyridazin-2-yl)acetamide. LC/MS (m/z): 437.1 (MH+), R1: 1.98 min; HPLC R1: 2.61 min.

Reference： [1]Patent: WO2007/95588,2007,A1 .Location in patent: Page/Page column 131

18
[ 101-84-8 ]
[ 121-43-7 ]
[ 108238-09-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 3483 - 3491

19
[ 108238-09-1 ]
[ 131703-53-2 ]
((CH₃)2CHO)2(C₆H₃)COOCH(COOH)(C₂HO₂B)(O)C₆H₄OC₆H₅ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 3483 - 3491

20
[ 1144508-53-1 ]
[ 108238-09-1 ]
[ 1144508-54-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; at 90℃;	((R)-2,4-dibenzylpiperazin-1-yl)(3-(2-phenoxyphenyl)thiophen-2-yl)methanone (R)-(3-bromothiophen-2-yl)(2,4-dibenzylpiperazin-1-yl)methanone (227.2 mg, 0.500 mmol) and <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (128.4 mg, 0.600 mmol) were suspended in Na2CO3 (2M aq., 0.9 mL, 1.80 mmol), EtOH (2 mL) and benzene (2 mL) under nitrogen atmosphere. Pd(PPh3)4 (58.0 mg, 0.0502 mmol) was added and the reaction mixture was tightly sealed and stirred at 90 C. overnight. It was extracted with ethyl acetate (2*3 mL) and the combined organic extracts were washed with brine (5 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a red oil (0.260 g, 95%). ESI-MS: m/z 545.4 (M+H)+.

Reference： [1]Patent: US2009/105251,2009,A1 .Location in patent: Page/Page column 54

21
[ 1144508-69-9 ]
[ 108238-09-1 ]
C₃₃H₃₅N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; copper diacetate; In dichloromethane; at 20℃;	Example 42 ((R)-2-benzylpiperazin-1-yl)(1-(2-phenoxyphenyl)-1H-pyrrol-2-yl)methanone (R)-tert-butyl 3-benzyl-4-(1H-pyrrole-2-carbonyl)piperazine-1-carboxylate (25 mg, 0.06 mmol) was dissolved in dichloromethane (0.5 mL) and Cu(Oac)2 (17 mg, 0.094 mmol) was added followed by <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (26.9 mg, 0.13 mmol) and pyridine (0.01 mL, 0.13 mmol). The reaction was allowed to stir at room temperature overnight. Excess dichloromethane (20 mL) was added and the solution was washed with water (25 mL) and brine (20 mL). The organics were collected, dried with sodium sulfate, and concentrated to an oil. The residue was taken up in dichloromethane (5 mL) and trifluoroacetic acid (2 mL) was added. The mixture was stirred at room temperature for 1 hour and then concentrated to an oil in vacuo. The residue was purified by HPLC (30-60% acetonitrile in water, TFA buffered) to afford the title compound as a white semisolid (27 mg, 66%). ESI-MS: m/z 438.4 (M+H)+.

Reference： [1]Patent: US2009/105251,2009,A1 .Location in patent: Page/Page column 67

22
[ 281225-12-5 ]
[ 108238-09-1 ]
[ 1198421-95-2 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 282 - 294

23
[ 108238-09-1 ]
(4-halo-3-methoxyphenyl)((1S,5R)-1,3,3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl)methanone [ No CAS ]
[ 1238635-39-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3742 - 3745

24
[ 1253201-80-7 ]
[ 108238-09-1 ]
C₃₂H₃₈N₄O₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 40 - 75℃;	3.5. 4-((S)-4-Carboxy-2-[2-(2-phenoxy-phenyl)-thiazole-4-carbonyl]-amino}-butyryl)- piperazine-1 -carboxylic acid butyl esterIntermediate 3.4 (15.2 mg) and <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (6.4 mg, 1.2 eq) were dissolved at 400C in a degassed mixture of EtOH/toluene (0.5 mL, 1:1) and aq. Na2CO3 (2M, 0.35 mL). Next, [Pd(PPh3)4] (0.05 eq) was added and the reaction mixture heated to 75C for 18 h. After cooling to RT, the crude product was subjected to saponification with aq. LiOH (2M, 0.3 mL) for 3 h at RT. The reaction mixture was directly purified by preparative HPLC (V) to give 15.9 mg of the desired product. LC-MS*: tR = 0.70 min; [M+H]+: 594.87.

Reference： [1]Patent: WO2010/122504,2010,A1 .Location in patent: Page/Page column 46

25
[ 209958-56-5 ]
[ 108238-09-1 ]
C₂₅H₂₂N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5480 - 5483

26
[ 108238-09-1 ]
[ 81290-20-2 ]
phenyl o-α,α,α-trifluorotolyl ether [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1174 - 1176

27
[ 1270083-99-2 ]
[ 108238-09-1 ]
[ 1270084-38-2 ]

Reference： [1]Synthesis,2011,p. 1783 - 1791

28
[ 1270083-97-0 ]
[ 108238-09-1 ]
[ 1270084-22-4 ]

Reference： [1]Synthesis,2011,p. 1783 - 1791

29
[ 1360612-58-3 ]
[ 108238-09-1 ]
[ 1360609-75-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In ethanol; toluene; at 120℃; for 1h;Inert atmosphere;	(4-Morpholin-4-yl-phenyl)-[8-(2-phenoxy-phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2- yl]-amine ("C289")To a solution of (8-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-yl-(4-morpholin-4-yl- phenyl)-amine (0.15 g, 0.45 mmol, 1 eq) in a mixture of ethanol : toluene (1 :4) (10 ml) is taken in a dry pressure tube, palladium acetate (0.01 g, 0.045 mmol, 0.1 eq), anhydrous potassium carbonate (0.125 g, 0.90 mmol, 2 eq), 2-dicyclo- hexylphosphino-2',6'-dimethoxybiphenyl, S-Phos (0.027 g, 0.06 mmol, 0.13 eq) and <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.19 g, 0.90 mmol, 2 eq) are added and the reaction mixture is degasified with nitrogen. The reaction mixture is heated to 120 C for 1 hour. The reaction mixture is concentrated and the residue is taken in 25% methanol in dichloromethane (50 ml) and filtered through celite to remove the inorganics and the filtrate is concentrated and purified by silica column using (230-400) mesh to get the product as pale yellow solid

Reference： [1]Patent: WO2012/25186,2012,A1 .Location in patent: Page/Page column 79-80; 182-183

30
[ 108238-09-1 ]
[ 2216-12-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1736 - 1739

31
[ 6628-86-0 ]
[ 108238-09-1 ]
[ 1299312-85-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate;tri-1-napthylphosphine; palladium dichloride; In tetrahydrofuran; at 65℃; for 15h;Microwave irradiation; Inert atmosphere; Reflux;	Example 6: Representative synthesis of 2-aminoindoles Scheme 10:Representative Procedures:Scheme 11 :31 A 20 mL capacity microwave vial was loaded with PdCl2 (0.05 equiv, 24 mg), P(l- naphthyl)3 (0.05 equiv, 56 mg), boronic acid 2 (2.0 equiv, 1.153 g), aldehyde 1 (1.0 equiv, 500 mg), K2C03 (3.0 equiv, 1.117 g), and dry THF (12 mL). The vial was sealed and purged with N2 for 5-10 min. The reaction mixture was heated at 65 C for 15 h, cooled to room temperature. Water was added and the reaction mixture was extracted with EtOAc (3 x 40 mL). The combined EtOAc extracts were dried over MgS04, filtered, concentrated in vacuo, and the residue obtained was dissolved in minimal amount of CH2C12 and loaded directly onto the ISCO (silica gel) column (0-20% EtOAc/hexanes) which gave diarylmethanol 3 (500 mg, yield: 52%) as a light yellow oil.

Reference： [1]Patent: WO2011/53697,2011,A1 .Location in patent: Page/Page column 78-80

32
[ 108238-09-1 ]
[ 1299312-87-0 ]

Reference： [1]Patent: WO2011/53697,2011,A1

33
[ 108238-09-1 ]
[ 1299312-86-9 ]

Reference： [1]Patent: WO2011/53697,2011,A1

34
[ 108238-09-1 ]
[ 1299312-88-1 ]

Reference： [1]Patent: WO2011/53697,2011,A1

35
[ 108238-09-1 ]
[ 1299309-78-6 ]

Reference： [1]Patent: WO2011/53697,2011,A1

36
[ 108238-09-1 ]
[ 106-51-4 ]
[ 1425038-43-2 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 2639 - 2648

37
[ 108238-09-1 ]
[ 1575-37-7 ]
[ 1430719-83-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3531 - 3545

38
[ 108238-09-1 ]
[ 1575-37-7 ]
[ 1430720-22-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3531 - 3545

39
[ 108238-09-1 ]
[ 29682-15-3 ]
[ 1431771-43-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3680 - 3688

40
[ 108238-09-1 ]
[ 1431771-45-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3680 - 3688

41
[ 108238-09-1 ]
[ 1431771-42-4 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3680 - 3688

42
[ 851684-46-3 ]
[ 108238-09-1 ]
[ 1432450-49-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3820 - 3832

43
[ 1445993-87-2 ]
[ 108238-09-1 ]
[ 1445992-62-0 ]

Yield	Reaction Conditions	Operation in experiment
59%		A mixture of Example le (152 mg, 0.40 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.111g, 0.520 mmol, 1.3 equivalents), Pd(PPh3)4 (0.023 g, 5 mol%) and cesium fluoride (0.182 g,1.2 mmol) in DME (3 mL) and methanol (1.5 mL) was heated under microwave condition(120 C, 30 minutes). To this mixture was added potassium carbonate (0.055 g, 0.40 mmol)and water (1 mL) and the reaction mixture was reheated in the microwave oven at 120 C foranother 2 hours. The organic layer was separated and purified by flash chromatography (silica gel, ethyl acetate). The resulting material was triturated with acetone and filtered to provide 0.075 g of the title compound (59%). 1H NMR (500 MHz, DMSO-d6) oe 3.50 (s, 3 H), 6.21-6.23 (m, 1 H), 6.88 (d, J=7.62 Hz, 2 H), 6.99-7.04 (m, 2 H), 7.24-7.30 (m, 5 H), 7.36-7.40(m, 1 H), 7.50 (dd, J=7.48, 1.68 Hz, 1H), 11.98 (s, 1 H). MS (ESI+)mlz 317 (M+H).
59%		A mixture of Example 1e (152 mg, 0.40 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.111 g, 0.520 mmol, 1.3 equivalents), Pd(PPh3)4 (0.023 g, 5 mol %) and cesium fluoride (0.182 g, 1.2 mmol) in DME (3 mL) and methanol (1.5 mL) was heated under microwave condition (120 C., 30 minutes). To this mixture was added potassium carbonate (0.055 g, 0.40 mmol) and water (1 mL) and the reaction mixture was reheated in the microwave oven at 120 C. for another 2 hours. The organic layer was separated and purified by flash chromatography (silica gel, ethyl acetate). The resulting material was triturated with acetone and filtered to provide 0.075 g of the title compound (59%). 1H NMR (500 MHz, DMSO-d6) delta 3.50 (s, 3H), 6.21-6.23 (m, 1H), 6.88 (d, J=7.62 Hz, 2H), 6.99-7.04 (m, 2H), 7.24-7.30 (m, 5H), 7.36-7.40 (m, 1H), 7.50 (dd, J=7.48, 1.68 Hz, 1H), 11.98 (s, 1H). MS (ESI+) m/z 317 (M+H)+.

Reference： [1]Patent: WO2013/97601,2013,A1 .Location in patent: Page/Page column 88; 89
[2]Patent: US2014/162971,2014,A1 .Location in patent: Paragraph 0746

44
[ 1445993-87-2 ]
[ 108238-09-1 ]
C₂₇H₂₂N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 120℃; for 0.5h;Microwave irradiation;	A mixture of Example le (152 mg, 0.40 rnmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.111 g, 0.520 mmol, 1.3 equivalents), Pd(PPh3)4 (0.023 g, 5 mol%) and cesium fluoride (0.182 g,1.2 mmol) in DME (3 mL) and methanol (1.5 mL) was heated under microwave condition (120 C, 30 minutes). To this mixture was added potassium carbonate (0.055 g, 0.40 mmol) and water (1 mL) and the reaction mixture was reheated in the microwave oven at 120 C for another 2 hours. The organic layer was separated and purified by flash chromatography (silica gel, ethyl acetate). The resulting material was triturated with acetone and filtered toprovide 0.075 g of the title compound (59%). 1H NMR (500 MHz, DMSO-d6) oe 3.50 (s, 3 H),6.2 1-6.23 (m, I H), 6.88 (d, J7.62 Hz, 2 H), 6.99-7.04 (m, 2 H), 7.24-7.30 (m, 5 H), 7.36-7.40 (m, I H), 7.50 (dd, J=7.48, 1.68 Hz, lH), 11.98 (s, 1 H). MS (ESI+) m/z 317 (M+H).

Reference： [1]Patent: WO2013/97052,2013,A1 .Location in patent: Page/Page column 58
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 8369 - 8384

45
[ 591-50-4 ]
[ 108238-09-1 ]
[ 6738-04-1 ]

Yield	Reaction Conditions	Operation in experiment
97%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

46
[ 540-38-5 ]
[ 108238-09-1 ]
[ 1469991-10-3 ]

Yield	Reaction Conditions	Operation in experiment
96%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Patent: WO2014/209034,2014,A1 .Location in patent: Paragraph 609; 610; 611
[2]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

47
[ 624-31-7 ]
[ 108238-09-1 ]
[ 1469991-11-4 ]

Yield	Reaction Conditions	Operation in experiment
97%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

48
[ 636-98-6 ]
[ 108238-09-1 ]
[ 1354828-74-2 ]

Yield	Reaction Conditions	Operation in experiment
93%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

49
[ 615-37-2 ]
[ 108238-09-1 ]
[ 1469991-12-5 ]

Yield	Reaction Conditions	Operation in experiment
91%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

50
[ 529-28-2 ]
[ 108238-09-1 ]
2-methoxy-2'-phenoxy-1,1-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

51
[ 533-58-4 ]
[ 108238-09-1 ]
2'-phenoxy-[1,1-biphenyl]-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

52
[ 615-43-0 ]
[ 108238-09-1 ]
[ 35883-09-1 ]

Yield	Reaction Conditions	Operation in experiment
12%Chromat.	With palladium; potassium hydroxide; In water; at 100℃; for 1h;Sealed tube; Green chemistry;	derivativesIn a typical synthesis, sealed tube of 10 mL capacity wascharged with aryl halide (1.0 mmol), (2-phenoxyphenyl) boronicacid (1.2 mmol)/(3-(dimethylamino)phenyl) boronic acid, KOH(2.0 mmol), Pd nanoplates solution (50 L, 0.0005 mmol) in aque-ous medium. The reaction mixture was heated at 100C for 1 h andthen allowed to cool at room temperature. Conversion of aryl halideand the formation of product were monitored by gas chromatog-raphy. The product was extracted with ethyl acetate (3 × 5 mL);died over Na2SO4and the solvent was evaporated under vacuum.The obtained crude product was then purified by column chro-matography using silica gel, (100-200 mesh size) with petroleumether/ethyl acetate (PE-EtOAc, 95:05) as eluent to give pure prod-uct. All products are confirmed by GC-MS (Shimadzu GC-MS QP2010). The representative products were characterized by1H NMRand13C NMR (Bruker UXNMR/XWIN-NMR (300 MHz) or Inova Var-ian VXR Unity (400, 500 MHz) instruments. Chemical shifts () arereported in ppm downfield from an internal TMS standard. Highresolution MS (HR-MS) data were recorded on a QSTAR XL HybridMS-MS mass spectrometer.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 30 - 37

53
[ 2586-62-1 ]
[ 108238-09-1 ]
2-methyl-1-(2-phenoxyphenyl)naphthalene [ No CAS ]
2-methyl-1-(2-phenoxyphenyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-[2'-(2,6-dimethoxyphenyl)-1,1'-binaphthalene-2-yl]diphenylphosphane; palladium diacetate; cesium fluoride; In tetrahydrofuran; for 72h;Reflux; Inert atmosphere;	General procedure: General procedure: A round bottom flask equipped with a magnetic stirrer bar and a condenser was charged with solid materials: boronic acid 7 (0.18mmol), base (0.3mmol), Pd(OAc)2 (0.005mmol, 1.12mg), and ligand (R)-1 (0.02mmol), and then purged three times under argon without any solvent. A solution of bromide 8 or 10 (0.1mmol) in solvent (1.25ml) was injected and this mixture was stirred for 72h at reflux unless said otherwise. After this time, the flask was allowed to warm to room temperature, after which dichloromethane (5ml) and water (5ml) were added to this mixture. The layers were separated and the aqueous layer was extracted with dichloromethane (3×5ml). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude mixture was purified by column chromatography over silica gel, to give the corresponding products. Enantiomeric excesses were determined by HPLC using Chiralcel OD-H, AD-H, or OJ-H (Daicel Chemical Industries) column.

Reference： [1]Tetrahedron Asymmetry,2013,vol. 24,p. 894 - 902

54
[ 3401-47-6 ]
[ 108238-09-1 ]
2-methoxy-1-(2-phenoxyphenyl)naphthalene [ No CAS ]
2-methoxy-1-(2-phenoxyphenyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-[2'-(2,6-dimethoxyphenyl)-1,1'-binaphthalene-2-yl]diphenylphosphane; palladium diacetate; cesium fluoride; In tetrahydrofuran; for 72h;Reflux; Inert atmosphere;	General procedure: General procedure: A round bottom flask equipped with a magnetic stirrer bar and a condenser was charged with solid materials: boronic acid 7 (0.18mmol), base (0.3mmol), Pd(OAc)2 (0.005mmol, 1.12mg), and ligand (R)-1 (0.02mmol), and then purged three times under argon without any solvent. A solution of bromide 8 or 10 (0.1mmol) in solvent (1.25ml) was injected and this mixture was stirred for 72h at reflux unless said otherwise. After this time, the flask was allowed to warm to room temperature, after which dichloromethane (5ml) and water (5ml) were added to this mixture. The layers were separated and the aqueous layer was extracted with dichloromethane (3×5ml). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude mixture was purified by column chromatography over silica gel, to give the corresponding products. Enantiomeric excesses were determined by HPLC using Chiralcel OD-H, AD-H, or OJ-H (Daicel Chemical Industries) column.

Reference： [1]Tetrahedron Asymmetry,2013,vol. 24,p. 894 - 902

55
[ 1473453-14-3 ]
[ 108238-09-1 ]
[ 1473453-11-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 20 - 120℃; for 0.5h;Microwave irradiation;	A 5 mE microwave reaction vessel equipped with stirbar was charged with Example 65d (0.078 g, 0.322 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.106 g, 0.495 mmol), 2 M aqueous sodium carbonate (1.6 mE, 3.20 mmol) and bis (triphenylphosphine)palladium(II) dichloride (0.015 g, 0.021 mmol) in ethanol (1.4 mE)DME (1.4 mE) and sealed. The mixture was heated at 120 C. for 30 minutes in a l3iotage Initiator 2 monomode microwave reactor, then cooled to ambient temperature. The mixture was shaken in a separatory funnel with SOmE ethyl acetate and SOmE brine. The organics were dried over anhydrous sodium sulfate. Afier filtration and solvent removal the residue was purified by reverse phase RPEC (Cl 8, 0-100% CR3 CNwater (0.1% TFA)) to afford the title compound. ?R NMR (300 MRz, CDC13) oe 9.15 (bs, 1R), 7.51 (m, 1R), 7.35 (m, 2R), 7.19 (m, 3R), 7.01 (d, J=2.7 Rz, 2R), 6.93 (m, 1R), 2.98 (m, 1R), 2.54 (s, 3R), 2.53 (m, 2R), 2.26 (m, 2R), 1.13 (d, J=3.2 Rz, 3R). MS (ESI+) mlz332.2 (M+R).
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 120℃; for 0.5h;Sealed tube; Microwave irradiation;	Example 65e. 3,6-dimethyl-l-(2-phenoxyphenyl)-2,5,6,7-tetrahydro-4H-isoindol-4-one. A 5 mL microwave reaction vessel equipped with stirbar was charged with Example 65 d (0.078 g, 0.322 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.106 g, 0.495 mmol), 2 M aqueous sodium carbonate (1.6 mL, 3.20 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.015 g, 0.021 mmol) in ethanol (1.4 mL)/DME (1.4 mL) and sealed. The mixture was heated at 120 C for 30 minutes in a Biotage Initiator 2 monomode microwave reactor, then cooled to ambient temperature. The mixture was shaken in a separatory funnel with 50 mL ethyl acetate and 50 mL brine. The organics were dried over anhydrous sodium sulfate. After filtration and solvent removal the residue was purified by reverse phase HPLC (CI 8, 0-100 %CH3CN/water (0.1% TFA)) to afford the title compound, H NMR (300 MHz, CDCI3) delta 9.15 (bs, 1H), 7.51 (m, 1H), 7.35 (m, 2H), 7.19 (m, 3H), 7.01 (d, J = 2.7 Hz, 2H), 6.93 (m, 1H), 2.98 (m, 1H), 2.54 (s, 3H), 2.53 (m, 2H), 2.26 (m, 2H), 1.13 (d, J = 3.2 Hz, 3H). MS (ESI+) m/z 332.2 (M+H)+.

Reference： [1]Patent: US2013/281450,2013,A1 .Location in patent: Paragraph 0350
[2]Patent: WO2013/155695,2013,A1 .Location in patent: Page/Page column 71

56
[ 10071-38-2 ]
[ 108238-09-1 ]
2-methyl-6-(2-phenoxyphenyl)pyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 120℃; for 0.666667h;Microwave irradiation;	A mixture of Example 1A (29 mg, 0.20 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.056 g, 0.260 mmol, 1.3 equivalents), Pd(PPh3)4 (0.011 g, 5 mol%) and cesium fluoride (0.091 g, 0.6 mmol) in DME (2 mL) and methanol (1 mL) was heated under microwave condition (120 C, 40 min.). The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgS04, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 30% ethyl acetate in hexanes to give the title compound (0.041 g, 74 % yield). 1H NMR (500 MHz, DMSO-d6) delta 7.75 (d, J = 9.77 Hz, 1H), 7.66 (dd, J = 7.78, 1.68 hz, 1H), 7.45-7.49 (m, 1H), 7.35-7.40 (m, 2H), 7.26-7.30 (m, 2H), 7.11-7.15 (m, 1 H), 6.97-7.01 (m, 3H), 6.94 (d, J = 9.77 Hz, 1H), 3.68 (s, 3H). MS (ESI+) m/z 279.0 (M+H)+.
74%	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 120℃; for 0.666667h;Microwave irradiation;	General procedure: Example 1B 2-methyl-6-(2-phenoxyphenyl)pyridazin-3(2H)-one [0724] A mixture of Example 1A (29 mg, 0.20 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.056 g, 0.260 mmol, 1.3 equivalents), Pd(PPh3)4 (0.011 g, 5 mol %) and cesium fluoride (0.091 g, 0.6 mmol) in DME (2 mL) and methanol (1 mL) was heated under microwave condition (120 C., 40 minutes). The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 30% ethyl acetate in hexanes to give the title compound (0.041 g, 74% yield). 1H NMR (500 MHz, DMSO-d6) delta 7.75 (d, J=9.77 Hz, 1H), 7.66 (dd, J=7.78, 1.68 hz, 1H), 7.45-7.49 (m, 1H), 7.35-7.40 (m, 2H), 7.26-7.30 (m, 2H), 7.11-7.15 (m, 1H), 6.97-7.01 (m, 3H), 6.94 (d, J=9.77 Hz, 1H), 3.68 (s, 3H). MS (ESI+) m/z 279.0 (M+H)+.

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 64; 65
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0724

57
4-(3-chloro-1-methyl-6-oxo-1,6-dihydropyridazin-4-yl)benzaldehyde [ No CAS ]
[ 108238-09-1 ]
4-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; at 120℃; for 1h;Inert atmosphere;	The product from Example 65A (0.249 g, 1.0 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.257 g, 1.2 mmol), bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.05 mmol) and sodium carbonate (1.0 mL, 2.0 mmol) were combined in 1 ,2-dimethoxyethane (4.0 mL), sparged with argon for 15 minutes and heated at 120 C for 60 minutes under argon. The mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2S04), treated with mercaptopropyl silica gel for twenty minutes, filtered and concentrated. Purification by chromatography (silica gel, 0-70% ethyl acetate in hexane) afforded the title compound (0.38 g, 94%>). 1H NMR (300 MHz, DMSO-d6) delta 9.98 (d, 1 H) 7.76 (d, J=8.48 Hz, 2 H) 7.62 (dd, J=7.46, 1.70 Hz, 1 H) 7.34 - 7.39 (m, 3 H) 7.15 - 7.26 (m, 3 H) 7.05 (d, J=7.12 Hz, 1 H) 7.01 (s, 1 H) 6.56 (d, J=8.14 Hz, 1 H) 6.32 (d, J=7.80 Hz, 2 H) 3.71 - 3.73 (m, 3 H). MS (ESI+) m/z 383 (M+H)+.
94%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; at 120℃; for 1h;Inert atmosphere;	Example 65B 4-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]benzaldehyde [0818] The product from Example 65A (0.249 g, 1.0 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.257 g, 1.2 mmol), bis(triphenylphosphine)palladium(II)chloride (0.035 g, 0.05 mmol) and sodium carbonate (1.0 mL, 2.0 mmol) were combined in 1,2-dimethoxyethane (4.0 mL), sparged with argon for 15 minutes and heated at 120 C. for 60 minutes under argon. The mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), treated with mercaptopropyl silica gel for twenty minutes, filtered and concentrated. Purification by chromatography (silica gel, 0-70% ethyl acetate in hexane) afforded the title compound (0.38 g, 94%). 1H NMR (300 MHz, DMSO-d6) delta 9.98 (d, 1H) 7.76 (d, J=8.48 Hz, 2H) 7.62 (dd, J=7.46, 1.70 Hz, 1H) 7.34-7.39 (m, 3H) 7.15-7.26 (m, 3H) 7.05 (d, J=7.12 Hz, 1H) 7.01 (s, 1H) 6.56 (d, J=8.14 Hz, 1H) 6.32 (d, J=7.80 Hz, 2H) 3.71-3.73 (m, 3H). MS (ESI+) m/z 383 (M+H)+

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 87
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0818

58
6-chloro-5-(4-(methoxymethyl)phenyl)-2-methylpyridazin-3(2H)-one [ No CAS ]
[ 108238-09-1 ]
5-[4-(methoxymethyl)phenyl]-2-methyl-6-(2-phenoxyphenyl)pyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 1h;Microwave irradiation;	A mixture of <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (323 mg, 1.5 11 mmol), Example 78A (100 mg, 0.378 mmol), potassium carbonate (157 mg, 1.133 mmol) and Pd(dppf)C12 (30.9 mg, 0.038 mmol) in 1 ,4-dioxane (2 mL) and water (0.5 mL) was heated in a microwave reactor at 100 C for 1 hour. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (4 x 30 mL). The organic layer was dried over anhydrous Na2504, filtered, and concentrated in vacuo. The residue was purified by preparative-TLC (silica, 100/1dichloromethane/methanol) followed by preparative HPLC (C 18, water (10 mM NH4HCO3)/acetonitrile, 35-75% gradient) to afford the title compound (73 mg, 49 % yield). ?HNMR(400MHz,DMSO-d6)5 11.80(s, 1 H), 8.64(s, 1 H), 8.63 (d,J= 4.4 Hz, 1 H), 7.76-7.80 (m, 2 H), 7.34-7.43 (m, 2 H), 6.70 (br s, 1 H), 6.25-6.28 (m, 1 H), 3.46 (s, 3 H),2.25 (s, 3 H), 2.04 (s, 3 H), 2.03 (s, 3 H). MS (ESI+) mlz 399 (M+H).
49%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 1h;Microwave irradiation;	General procedure: Example 78B 5-[4-(methoxymethyl)phenyl]-2-methyl-6-(2-phenoxyphenyl)pyridazin-3(2H)-one [0833] A mixture of <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (323 mg, 1.511 mmol), Example 78A (100 mg, 0.378 mmol), potassium carbonate (157 mg, 1.133 mmol) and Pd(dppf)Cl2 (30.9 mg, 0.038 mmol) in 1,4-dioxane (2 mL) and water (0.5 mL) was heated in a microwave reactor at 100 C. for 1 hour. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (4×30 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by preparative-TLC (silica, 100/1 dichloromethane/methanol) followed by preparative HPLC (C18, water (10 mM NH4HCO3)/acetonitrile, 35-75% gradient) to afford the title compound (73 mg, 49% yield). 1H NMR (400 MHz, DMSO-d6) delta 11.80 (s, 1H), 8.64 (s, 1H), 8.63 (d, J=4.4 Hz, 1H), 7.76-7.80 (m, 2H), 7.34-7.43 (m, 2H), 6.70 (br s, 1H), 6.25-6.28 (m, 1H), 3.46 (s, 3H), 2.25 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H). MS (ESI+) m/z 399 (M+H)+

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 91
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0833

59
tert-butyl 4-(3-chloro-1-methyl-6-oxo-1,6-dihydropyridazin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
[ 108238-09-1 ]
tert-butyl 4-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 130℃; for 2h;Microwave irradiation;	A mixture of <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (197 mg, 0.921 mmol), Example 81A (100 mg, 0.307 mmol), potassium carbonate (127 mg, 0.921 mmol) and Pd(dppf)Cl2 (25.1 mg, 0.031 mmol) in dioxane (3 mL) and water (0.75 mL) was heated under microwave conditions at 130 C for 2 hours. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (2 x 10 mL). The organic layer was dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 6: 1 to 3: 1 gradient, petroleum ether/ethyl acetate) to afford the title compound (0.070 g, 47 % yield). 1H NMR (400 MHz, CDC13) delta 7.42 (d, J= 7.2 Hz, 1 H), 7.37-7.27 (m, 3 H ), 7.18 (t, J = 7.2 Hz, 1 H), 7.08 (t, J= 7.2 Hz, 1 H), 6.87 (t, J= 7.2 Hz, 3 H), 6.73 (s, 1 H), 5.56 (s, 1 H), 3.81-3.77 (m, 5 H ), 3.38 (s, 2 H), 2.09 (s, 2 H), 1.46 (s, 9 H). MS (ESI+) m/z 460.0 (M+H)+.
47%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 130℃; for 2h;Microwave irradiation;	Example 81B tert-butyl 4-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]-3,6-dihydropyridine-1(2H)-carboxylate [0839] A mixture of <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (197 mg, 0.921 mmol), Example 81A (100 mg, 0.307 mmol), potassium carbonate (127 mg, 0.921 mmol) and Pd(dppf)Cl2 (25.1 mg, 0.031 mmol) in dioxane (3 mL) and water (0.75 mL) was heated under microwave conditions at 130 C. for 2 hours. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (2×10 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 6:1 to 3:1 gradient, petroleum ether/ethyl acetate) to afford the title compound (0.070 g, 47% yield). 1H NMR (400 MHz, CDCl3) delta 7.42 (d, J=7.2 Hz, 1H), 7.37-7.27 (m, 3H), 7.18 (t, J=7.2 Hz, 1H), 7.08 (t, J=7.2 Hz, 1H), 6.87 (t, J=7.2 Hz, 3H), 6.73 (s, 1H), 5.56 (s, 1H), 3.81-3.77 (m, 5H), 3.38 (s, 2H), 2.09 (s, 2H), 1.46 (s, 9H). MS (ESI+) m/z 460.0 (M+H)+

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 92
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0839

60
[ 108238-09-1 ]
[ 2417-10-9 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 7291 - 7294

61
C₁₇H₂₁ClN₄O [ No CAS ]
[ 108238-09-1 ]
[ 76-05-1 ]
2-methyl-5-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}-6-(2-phenoxyphenyl)pyridazin-3(2H)-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Syntheses were performed using a Personal Chemistry Ermy?s optimizer microwave. . Each microwave tube was charged with a stir bar and 0.1 equivalent of PdC12(PPh3)2 (15mg).. In the microwave tube, a solution of Example 1 8B (3 9mg, 0.22mmol) dissolved in dioxane (1.0 mL) was added, followed by the additionof 1-methyl-4-(3-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine (82 mg,0.26mmol) in dioxane(0.7mL). Then, 434 iL of 1M aqueous solution of Cs2CO3 was added. The resulting mixture was heated in the microwave for 1800 seconds at 150 C. In the microwave vial with the previous mixture a solution of <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (26mg, 0.12 mmol) in dioxane(0 .5 mL), was added, along with 0.1 equivalent of PdC12(PPh3)2 (9 mg)and 246 iL of 1M aqueous solution of Cs2CO3. This was capped and placed back in the microwave to heat for 1800 seconds at 150 C. The reaction mixture was filtered, and concentrated to dryness. The residues were dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (C 18, CH3CN/water (0.1 %TFA), 0-100% gradient) provided the title compound as TFA salt. ?H NMR (500 MHz, DMSO-d6) oe 7.67 (dd, J = 7.63, 1.53 Hz, 1H), 7.29-7.39 (m, 4H), 7.22-7.26 (m, 3H), 7.01-7.15 (m, 3H), 6.94 (s, 1H), 6.91 (s, 1H), 6.54 (d, J = 7.93 Hz, 1H), 6.32 (d, J = 7.63 Hz, 1H), 3.73 (s, 3H), 3.52 (s, 2H), 2.77 (s, 3H). MS (ESI) mlz 467 (M+H).

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 84; 85

62
[ 108238-09-1 ]
[ 89488-30-2 ]
[ 76-05-1 ]
3-methyl-5-(2-phenoxyphenyl)pyridin-2(1H)-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%		2-Phenoxylphenylboronic acid (0.072 g, 0.335 mmol), 5-bromo-3-methylpyridin-2(lH)-one (0.060 g, 0.319 mmol), bis(triphenylphosphine)palladium(II) chloride (0.009 g, 0.013 mmol) and 2M sodium carbonate (0.64 mL, 1.28 mmol) were combined in 1 ,2-dimethoxyethane (1.6 mL) and ethanol (1.6 mL), sparged with nitrogen for 15 minutes and heated by microwave at 120 C for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried (Na2S04), filtered and concentrated. Purification by reverse phase HPLC (CI 8, 0-100 % CH3CN/water (0.1% TFA)) afforded the title compound as the trifluoroacetic acid salt (0.020 g, 23%). 1H NMR (300 MHz, DMSO-d6) 5 11.60 (s, 1 H) 6.75 - 7.63 (m, 11 H) 1.97 (m, 3 H) MS (APCI+) m/z 278 (M+H)+.
23%		Example 260 3-methyl-5-(2-phenoxyphenyl)pyridin-2(1H)-one [1086] 2-Phenoxylphenylboronic acid (0.072 g, 0.335 mmol), 5-bromo-3-methylpyridin-2(1H)-one (0.060 g, 0.319 mmol), bis(triphenylphosphine)palladium(II)chloride (0.009 g, 0.013 mmol) and 2M sodium carbonate (0.64 mL, 1.28 mmol) were combined in 1,2-dimethoxyethane (1.6 mL) and ethanol (1.6 mL), sparged with nitrogen for 15 minutes and heated by microwave at 120 C. for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried (Na2SO4), filtered and concentrated. Purification by reverse phase HPLC (C18, 0-100% CH3CN/water (0.1% TFA)) afforded the title compound as the trifluoroacetic acid salt (0.020 g, 23%). 1H NMR (300 MHz, DMSO-d6) delta 11.60 (s, 1H) 6.75-7.63 (m, 11H) 1.97 (m, 3H) MS (APCI+) m/z 278 (M+H)+

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 147
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 1086
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 8369 - 8384

63
methyl 1-(3-chloro-1-methyl-6-oxo-1,6-dihydropyridazin-4-yl)pyrrolidine-3-carboxylate [ No CAS ]
[ 108238-09-1 ]
methyl 1-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]pyrrolidine-3-carboxylate [ No CAS ]
ethyl 1-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]pyrrolidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 90℃;Inert atmosphere;	General procedure: Example 1 A (0.145 g, 1 mmol), 2-fluoro-5-nitrophenylboronic acid (0.294 g, 1.1 mmol), Pd(PPh3)4 (0.058 g, 0.05 mmol) and sodium carbonate (0.212 g, 2.0 mmol) were combined in toluene (4 mL), ethanol (1 mL), and water (1 mL) and the mixture was degassed and left under nitrogen. The reaction mixture was heated at 90 C overnight, and then cooled to room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgS04), filtered and concentrated. The crude product was purified by flash chromatography (silica gel, 20-50% ethyl acetate in hexanes) to provide 0.19 g (76%) of the title compound. Example 48B was prepared according to the procedure used for the preparation of Example 9A, substituting Example 48A for Example 1A, and substituting <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> for 2-fluoro-5-nitrophenylboronic acid, respectively, to provide the title compound. 1H NMR (500 MHz, DMSO- 6) delta 7.43-7.48 (m, 2H), 7.33-7.36 (m, 2H), 7.32-7.38 (m, 1H), 7.11 (t, J = 7.32 Hz, 1H), 6.92-6.93 (m, 3H), 5.64 (s, 1H), 4.82 (s, 2H), 3.59 (s, 3H), 3.46 (s, 3H)3.00-3.15 (m, 5H), 1.99-2.06 (m, 2H). MS (DCI+) m/z 406.1 (M+H)+. 49. ethyl l-[l-methyl-6-oxo-3-(2-phenoxyphenyl)-l,6-dihydro yridazin-4- yl]pyrrolidine-3-carboxylate. Example 49 was isolated as a by-product during the formation of Example 48B. 1H NMR (500 MHz, DMSO-d6) delta 7.42-7.48 (m, 2H), 7.33-7.36 (m, 2H), 7.22 (t, J = 7.48 Hz, 1H), 7.12 (t, J = 7.32 Hz, 1H), 6.91-6.92 (m, 3H), 5.64 (s, 1H), 4.02-4.07 (s, 2H), 3.46 (s, 3H), 3.02-3.17 (m, 5H), 1.84-2.08 (m, 2H), 1.13 (t, J = 7.02 Hz, 3H). MS (DCI+) m/z 420.2 (M+H)+.

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 68; 80

64
C₁₄H₁₃ClN₂O₃ [ No CAS ]
[ 108238-09-1 ]
ethyl 3-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.11 g	In tetrahydrofuran; ethanol; water;Reflux; Inert atmosphere;	Example 18B (0.090 g, 0.5 mmol), 3-(ethoxycarbonyl)phenylboronic acid (0.107 g, 0.55 mmol), Pd(PPh3)4 (0.058 g, 0.05 mmol) and sodium carbonate (0.106 g, 1.0 mmol) were combined in toluene (4 mL), ethanol (1 mL) and water (1 mL) and the mixture was degassed and left under nitrogen. The reaction mixture was heated at 90 C for 2 hours, and then cooled to room temperature. To this solution was he added <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.150 g, 1.4 mmol). The reaction mixture was heated under reflux overnight. After cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried (MgS04), filtered and concentrated. The crude product was purified by flash chromatography (silica gel, 20-50% ethyl acetate in hexanes) to provide crude material, which was further purified by reverse HPLC (C18, CH3CN/water (0.1%TFA), 0-100%) to afford 0.11 g (52%) of the title compound. 1H NMR (500 MHz, DMSO- d6) delta 7.90-7.92 (m, 1H), 7.67 (s, 1H), 7.61 (dd, J = 7.63, 1.83 Hz, 1H), 7.40-7.46 (m, 2H), 7.19- 7.24 (m, 3H), 7.32-7.35 (m, 1H), 7.17-7.23 (m, 3H), 7.03 (t, J = 7.32 Hz, 1H), 7.00 (s, 1H), 6.56 (d, J = 8.24 Hz, 1H), 6.32 (d, J = 7.63 Hz, 2H), 4.21 (q, J = 7.12 Hz, 2H), 3.73 (s, 3H), 1.23 (t, J = 7.02 Hz, 3H). MS (DCI+) m/z 427.1 (M+H)+.

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 84

65
5-chloro-4-methoxy-1-methylpyridin-2(1H)-one [ No CAS ]
[ 108238-09-1 ]
4-methoxy-1-methyl-5-(2-phenoxyphenyl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With palladium diacetate; cesium fluoride; DavePhos; In 1,4-dioxane; at 90℃;Inert atmosphere;	A mixture of Example 258A (0.035 g, 0.2 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.064 g, 0.30 mmol), 2'- (dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (0.016 g, 0.040 mmol), palladium(II) acetate (0.0045 g, 0.02 mmol) and CsF (0.091 g, 0.6 mmol) in dioxane (1 mL) in a 4 mL vial was degassed and back-filled with nitrogen four times. The reaction mixture was heated at 90 C overnight. The mixture was filtered through a pad of filtering agent. The filtrate was concentrated. The residue was then purified by reverse HPLC (C 18, CH3CN/water (0.1%TFA), 0-100%) to afford 0.030 g (48%) of the title compound. 1H NMR (500 MHz, DMSO-dg) delta 7.57 (m, 1H), 7.30-7.37 (m, 4H), 7.16-7.20 (m, 1H), 7.07 (t, J = 7.32 Hz, 1H), 6.90-6.92.(m, 3H), 5.79 (s, 1H), 3.54 (s, 3H), 3.34 (s, 3H). MS (ESI+) m/z 308.1 (M+H)+.
48%	With palladium diacetate; cesium fluoride; DavePhos; In 1,4-dioxane; at 90℃;Inert atmosphere;	General procedure: Example 258B 4-methoxy-1-methyl-5-(2-phenoxyphenyl)pyridin-2(1H)-one [1081] A mixture of Example 258A (0.035 g, 0.2 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.064 g, 0.30 mmol), 2?-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (0.016 g, 0.040 mmol), palladium(II)acetate (0.0045 g, 0.02 mmol) and CsF (0.091 g, 0.6 mmol) in dioxane (1 mL) in a 4 mL vial was degassed and back-filled with nitrogen four times. The reaction mixture was heated at 90 C. overnight. The mixture was filtered through a pad of filtering agent. The filtrate was concentrated. The residue was then purified by reverse HPLC (C18, CH3CN/water (0.1% TFA), 0-100%) to afford 0.030 g (48%) of the title compound. 1H NMR (500 MHz, DMSO-d6) delta 7.57 (m, 1H), 7.30-7.37 (m, 4H), 7.16-7.20 (m, 1H), 7.07 (t, J=7.32 Hz, 1H), 6.90-6.92. (m, 3H), 5.79 (s, 1H), 3.54 (s, 3H), 3.34 (s, 3H). MS (ESI+) m/z 308.1 (M+H)+

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 146
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 1081

66
N-(4-(3-chloro-1-methyl-6-oxo-1,6-dihydropyridazin-4-yl)phenyl)acetamide [ No CAS ]
[ 108238-09-1 ]
N-{4-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]phenyl}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 1,4-dioxane; water; at 135℃; for 0.5h;Microwave irradiation;	A 4mL microwave vial was charged with a stir bar, a solution of Example 18B (40 mg, 0.22 mmol) in dioxane (lmL), a solution of N-(4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl)acetamide monomer (87 mg, 1.5 equivalents,0.34 mmol) in dioxane (1 mL), cesium carbonate (145 mg, 2 eq, 0.44 mmol) in water (.45 mL) with Silicat resin (82 mg, 0.1 eq, 0.27 loading). This was placed in parallel dual model microwave system Anton Parr and was allowed to heat at 135 C for 30 minutes. Upon completion, the crude material was filtered, dried, and purified by reverse phase HPLC (CI 8, 0-100 % CH3CN/water (0.1% TFA)) to afford N-(4-(3-chloro-l-methyl-6-oxo-l,6-dihydropyridazin-4- yl)phenyl)acetamide intermediate (35 mg, 0.13 mmol) which was then dissolved in dioxane ( lmL) to which was added excess 2-pheoxyphenyl boronic acid (45 mg, 1.6 equivalents, 0.20mmol) in dioxane, cesium carbonate (41 mg, 1 equivalent, 0.12 mmol) in water (0.130 mL) and with Silicat resin (93 mg, 0.2 eq, 0.27 loading). This was again placed in parallel dual model microwave system Anton Parr and was allowed to heat at 135 C for 30 minutes. Upon completion, the crude material was filtered, dried, and purified by reverse phase HPLC (CI 8, 0-100 % CH3CN/water (0.1% TFA)) to afford the title compound. 1H NMR (400 MHz, DMSO-d6/D20) delta 7.58 (dd, J = 7.5, 1.7 Hz, 1H), 7.48-7.32 (m, 3H), 7.25-7.16 (m, 3H), 7.06 (t, J = 7.9 Hz, 3H), 6.89 (s, 1H), 6.57 (d, J = 7.7 Hz, 1H), 6.36 (d, J = 7.7 Hz, 2H), 3.70 (s, 3H), 2.06 (s, 3H). MS (ESI+) m/z 412 (M+H)+.
	With caesium carbonate; In 1,4-dioxane; water; at 135℃; for 0.5h;Microwave irradiation;	General procedure: Example 105 N-{4-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]phenyl}acetamide [0875] A 4 mL microwave vial was charged with a stir bar, a solution of Example 18B (40 mg, 0.22 mmol) in dioxane (1 mL), a solution of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide monomer (87 mg, 1.5 equivalents, 0.34 mmol) in dioxane (1 mL), cesium carbonate (145 mg, 2 eq, 0.44 mmol) in water (0.45 mL) with Silicat resin (82 mg, 0.1 eq, 0.27 loading). This was placed in parallel dual model microwave system Anton Parr and was allowed to heat at 135 C. for 30 minutes. Upon completion, the crude material was filtered, dried, and purified by reverse phase HPLC (C18, 0-100% CH3CN/water (0.1% TFA)) to afford N-(4-(3-chloro-1-methyl-6-oxo-1,6-dihydropyridazin-4-yl)phenyl)acetamide intermediate (35 mg, 0.13 mmol) which was then dissolved in dioxane (1 mL) to which was added excess 2-pheoxyphenyl boronic acid (45 mg, 1.6 equivalents, 0.20 mmol) in dioxane, cesium carbonate (41 mg, 1 equivalent, 0.12 mmol) in water (0.130 mL) and with Silicat resin (93 mg, 0.2 eq, 0.27 loading). This was again placed in parallel dual model microwave system Anton Parr and was allowed to heat at 135 C. for 30 minutes. Upon completion, the crude material was filtered, dried, and purified by reverse phase HPLC (C18, 0-100% CH3CN/water (0.1% TFA)) to afford the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) delta 7.58 (dd, J=7.5, 1.7 Hz, 1H), 7.48-7.32 (m, 3H), 7.25-7.16 (m, 3H), 7.06 (t, J=7.9 Hz, 3H), 6.89 (s, 1H), 6.57 (d, J=7.7 Hz, 1H), 6.36 (d, J=7.7 Hz, 2H), 3.70 (s, 3H), 2.06 (s, 3H). MS (ESI+) m/z 412 (M+H)+.

Reference： [1]Patent: WO2013/185284,2013,A1 .Location in patent: Page/Page column 100; 101
[2]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0875

67
[ 883738-27-0 ]
[ 108238-09-1 ]
[ 76-05-1 ]
[ 6794-35-0 ]
2-methyl-5-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}-6-(2-phenoxyphenyl)pyridazin-3(2H)-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Example 60 2-methyl-5-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}-6-(2-phenoxyphenyl)pyridazin-3(2H)-one [0807] Syntheses were performed using a Personal Chemistry Ermy's optimizer microwave. Each microwave tube was charged with a stir bar and 0.1 equivalent of PdCl2(PPh3)2 (15 mg). In the microwave tube, a solution of Example 18B (39 mg, 0.22 mmol) dissolved in dioxane (1.0 mL) was added, followed by the addition of 1-methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine (82 mg, 0.26 mmol) in dioxane (0.7 mL). Then, 434 muL of 1M aqueous solution of Cs2CO3 was added. The resulting mixture was heated in the microwave for 1800 seconds at 150 C. In the microwave vial with the previous mixture a solution of <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (26 mg, 0.12 mmol) in dioxane (0.5 mL), was added, along with 0.1 equivalent of PdCl2(PPh3)2 (9 mg) and 246 muL of 1M aqueous solution of Cs2CO3. This was capped and placed back in the microwave to heat for 1800 seconds at 150 C. The reaction mixture was filtered, and concentrated to dryness. The residues were dissolved in 1:1 DMSO/ MeOH. Purification by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 0-100% gradient) provided the title compound as TFA salt. 1H NMR (500 MHz, DMSO-d6) delta 7.67 (dd, J=7.63, 1.53 Hz, 1H), 7.29-7.39 (m, 4H), 7.22-7.26 (m, 3H), 7.01-7.15 (m, 3H), 6.94 (s, 1H), 6.91 (s, 1H), 6.54 (d, J=7.93 Hz, 1H), 6.32 (d, J=7.63 Hz, 1H), 3.73 (s, 3H), 3.52 (s, 2H), 2.77 (s, 3H). MS (ESI) m/z 467 (M+H)+

Reference： [1]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0807

68
[ 22237-12-3 ]
[ 108238-09-1 ]
[ 76-05-1 ]
[ 6794-35-0 ]
5-(3-amino-4-methylphenyl)-2-methyl-6-(2-phenoxyphenyl)pyridazin-3(2H)-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 64 5-(3-amino-4-methylphenyl)-2-methyl-6-(2-phenoxyphenyl)pyridazin-3(2H)-one [0816] Example 64 was prepared according to the procedure used for the preparation of Example 60, substituting 3-amino-4-methylphenylboronic acid for 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine, to provide the title compound as TFA salt. 1H NMR (500 MHz, DMSO-d6) delta 7.57 (dd, J=7.63, 1.53 Hz, 1H) 7.33-7.40 (m, 1H) 7.20-7.26 (m, 3H) 7.00-7.11 (m, 2H) 6.90 (d, J=1.53 Hz, 1H) 6.86 (s, 1H) 6.68 (dd, J=7.93, 1.53 Hz, 1H) 6.59 (d, J=7.63 Hz, 1H) 6.38 (d, J=7.63 Hz, 2H) 3.70 (s, 3H) 2.19 (s, 3H). MS (ESI) m/z 384 (M+H)+.

Reference： [1]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0816

69
[ 10071-38-2 ]
[ 64-17-5 ]
[ 108238-09-1 ]
methyl 1-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]pyrrolidine-3-carboxylate [ No CAS ]
ethyl 1-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]pyrrolidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 90℃;Inert atmosphere;	Example 48B methyl 1-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]pyrrolidine-3-carboxylate [0787] Example 48B was prepared according to the procedure used for the preparation of Example 9A, substituting Example 48A for Example 1A, and substituting <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> for 2-fluoro-5-nitrophenylboronic acid, respectively, to provide the title compound. 1H NMR (500 MHz, DMSO-d6) delta 7.43-7.48 (m, 2H), 7.33-7.36 (m, 2H), 7.32-7.38 (m, 1H), 7.11 (t, J=7.32 Hz, 1H), 6.92-6.93 (m, 3H), 5.64 (s, 1H), 4.82 (s, 2H), 3.59 (s, 3H), 3.46 (s, 3H) 3.00-3.15 (m, 5H), 1.99-2.06 (m, 2H). MS (DCI+) m/z 406.1 (M+H)+. Example 49 ethyl 1-[1-methyl-6-oxo-3-(2-phenoxyphenyl)-1,6-dihydropyridazin-4-yl]pyrrolidine-3-carboxylate [0788] Example 49 was isolated as a by-product during the formation of Example 48B. 1H NMR (500 MHz, DMSO-d6) delta 7.42-7.48 (m, 2H), 7.33-7.36 (m, 2H), 7.22 (t, J=7.48 Hz, 1H), 7.12 (t, J=7.32 Hz, 1H), 6.91-6.92 (m, 3H), 5.64 (s, 1H), 4.02-4.07 (s, 2H), 3.46 (s, 3H), 3.02-3.17 (m, 5H), 1.84-2.08 (m, 2H), 1.13 (t, J=7.02 Hz, 3H). MS (DCI+) m/z 420.2 (M+H)+.

Reference： [1]Patent: US2013/331382,2013,A1 .Location in patent: Paragraph 0787-0788

70
[ 1193-21-1 ]
[ 108238-09-1 ]
[ 954221-95-5 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3939 - 3965

71
[ 108238-09-1 ]
[ 1606169-33-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3939 - 3965

72
1-bromo-3-methyl-6,7-dihydro-2H-pyrrolo[3,4-c]pyridin-4(5H)-one [ No CAS ]
[ 108238-09-1 ]
3-methyl-1-(2-phenoxyphenyl)-2,5,6,7-tetrahydro-4H-pyrrolo[3,4-c]pyridin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; at 120℃; for 0.5h;Sealed tube;	3-methyl-1-(2-phenoxyphenyl)-6,7-dihydro-2H-pyrrolo[3,4-c]pyridin-4(5H)-one A 2 mL microwave reaction vessel equipped with stirbar was charged with Example 92f (0.010 g, 0.044 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.023 g, 0.109 mmol), 2 M aqueous sodium carbonate (0.218 mL, 0.437 mmol) and bis(triphenylphosphine)palladium(II) dichloride (3.06 mg, 4.37 mumol) in ethanol (0.200 mL)/DME (0.200 mL) and sealed. The mixture was heated at 120 C. for 30 minutes in a Biotage Initiator 2 monomode microwave reactor, then cooled to ambient temperature. The mixture was shaken in a separatory funnel with 75 mL ethyl acetate and 50 mL saturated aqueous sodium chloride. The organics were dried over anhydrous sodium sulfate. After filtration and solvent removal the residue was purified by reverse phase HPLC (C18, 0-100% CH3CN/water (0.1% TFA)) to afford the title compound (7.3 mg, 53%). 1H NMR (300 MHz, CD3OD) delta 10.74 (bds, 1H), 7.42 (dd, J=1.9, 7.6 Hz, 1H), 7.31-7.18 (m, 4H), 7.02-6.96 (m, 2H), 6.85 (m, 2H), 3.36 (m, 2H), 2.73 (m, 2H), 2.44 (s, 3H). MS (ESI+) m/z 319.2 (M+H)+.

Reference： [1]Patent: US2014/256705,2014,A1 .Location in patent: Paragraph 0659

73
methyl 1-bromo-3-methyl-4-oxo-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate [ No CAS ]
[ 108238-09-1 ]
3-methyl-4-oxo-1-(2-phenoxyphenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In methanol; 1,2-dimethoxyethane; at 120℃; for 0.5h;Sealed tube; Microwave irradiation;	Example 97e 3-methyl-4-oxo-1-(2-phenoxyphenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid A 5 mL microwave reaction vessel equipped with stirbar was charged with Example 97d (0.072 g, 0.173 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.121 g, 0.565 mmol), 2 M aqueous sodium carbonate (0.86 mL, 1.720 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.0128 g, 0.018 mmol) in methanol (0.782 mL)/DME (0.782 mL) and sealed. The mixture was heated at 120 C. for 30 minutes in a Biotage Initiator 2 monomode microwave reactor, and then cooled to ambient temperature. The mixture was shaken in a separatory funnel with 75 mL ethyl acetate and 50 mL saturated aqueous sodium chloride. The aqueous phase was acidified with HCl and extracted with 75 mL ethyl acetate. The organics were dried over anhydrous sodium sulfate. Filtration and solvent removal provided the title compound.

Reference： [1]Patent: US2014/256705,2014,A1 .Location in patent: Paragraph 0682

74
3-iodo-7-methoxy-1H-pyrrolo[2,3-c]pyridine [ No CAS ]
[ 108238-09-1 ]
7-methoxy-3-(2-phenoxyphenyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.6%	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 120℃; for 0.5h;Microwave irradiation;	Example 1A 7-methoxy-3-(2-phenoxyphenyl)-1H-pyrrolo[2,3-c]pyridine [0825] A mixture of 3-iodo-7-methoxy-1H-pyrrolo[2,3-c]pyridine (0.274 g, 1.0 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.278 g, 1.3 mmol, 1.3 equivalents), Pd(PPh3)4 (0.058 g, 0.05 mmol), and cesium fluoride (0.456 g, 3 mmol) in dimethxoyethane (3 mL) and methanol (1.5 mL) was heated under microwave conditions (120 C., 30 minutes). The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate/hexanes) to give the title compound (0.122 g, 38.6% yield).

Reference： [1]Patent: US2014/275026,2014,A1 .Location in patent: Paragraph 0825

75
[ 108238-09-1 ]
7-methoxy-1-methyl-3-(2-phenoxyphenyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Reference： [1]Patent: US2014/275026,2014,A1

76
[ 108238-09-1 ]
1-methyl-3-(2-phenoxyphenyl)-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one [ No CAS ]

Reference： [1]Patent: US2014/275026,2014,A1

77
[ 201230-82-2 ]
[ 108238-09-1 ]
bis(2-phenoxyphenyl)methanone [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2014,vol. 9,p. 2411 - 2414,4

78
methyl 1-bromo-3-methyl-4-oxo-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate [ No CAS ]
[ 108238-09-1 ]
methyl 3-methyl-4-oxo-1-(2-phenoxyphenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; sodium carbonate; bis(dibenzylideneacetone)-palladium(0); In water; at 20 - 60℃;Inert atmosphere;	Example 1f methyl 3-methyl-4-oxo-1-(2-phenoxyphenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate Example 1e (0.083 g, 0.2 mmol), <strong>[108238-09-1]2-phenoxyphenylboronic acid</strong> (0.064 g, 0.3 mmol), bis(dibenzylideneacetone)palladium(0) (0.0055 g, 6 mumol), (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (0.0064 g, 0.022 mmol) and sodium carbonate (0.106 g, 1 mmol) were combined and sparged with nitrogen for 40 minutes. Nitrogen-sparged dioxane (1 mL) and water (0.250 mL) were added. The mixture was stirred at 60 C. for five hours and then at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 25-55% ethyl acetate in hexanes) to give 0.03 g (30%) of the title compound.

Reference： [1]Patent: US2014/256705,2014,A1 .Location in patent: Paragraph 0495

79
[ 108238-09-1 ]
methyl 3-methyl-4-oxo-1-(2-phenoxyphenyl)-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/256705,2014,A1

80
[ 108238-09-1 ]
3-methyl-4-oxo-1-(2-phenoxyphenyl)-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2014/256705,2014,A1

81
[ 13675-18-8 ]
[ 2688-84-8 ]
[ 108238-09-1 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 10568 - 10580

82
[ 108238-09-1 ]
4-(2'-phenoxybiphenyl-4-yloxy)butyric acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2014/209034,2014,A1

83
[ 108238-09-1 ]
4-(2'-phenoxybiphenyl-4-yloxy)butyric acid [ No CAS ]

Reference： [1]Patent: WO2014/209034,2014,A1

84
3-iodo-4,5-diphenyl-2-(2-(phenylsulfonyl)ethyl)furan [ No CAS ]
[ 108238-09-1 ]
3-(2-phenoxyphenyl)-4,5-diphenyl-2-(2-(phenylsulfonyl)ethyl)furan [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 5896 - 5900

85
[ 108238-09-1 ]
4-(benzo[d][1,3]dioxo-5-yl)-4-(2-phenoxyphenyl)butan-2-one [ No CAS ]
4-(benzo[d][1,3]dioxo-5-yl)-4-(2-phenoxyphenyl)butan-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 9931 - 9935
Angew. Chem.,2015,vol. 127,p. 9861 - 10172,312

86
[ 108238-09-1 ]
potassium trifluoro(2-phenoxyphenyl)borate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 9931 - 9935
Angew. Chem.,2015,vol. 127,p. 9861 - 10172,312

87
[ 5419-55-6 ]
[ 7025-06-1 ]
[ 108238-09-1 ]

Yield	Reaction Conditions	Operation in experiment
80%		The 1-bromo-2-phenoxybenzene 0.018 muM is dissolved in 100 ml, in dry THF, added after the never-dried 500 ml three-mouth bottle, N2 -78 °C under the protection of the reaction 30min, slow adds by drops positively BuLi 0.027 muM, after dropping maintain -78 °C reaction 3h, then slowly dropping triisopropyl borate 0.02 muM, after dropping the reaction is maintained in the -78 °C reaction 2h, slow heating to room temperature, the reaction overnight, TLC monitoring after the reaction is completed, water slow quenching the reaction solution, extraction to dryness, to obtain 2-phenoxyphenylboronic acid (B-1) 0.0144 muM, and the yield is 80percent. Mass spectrum: 214.06.

Reference： [1]Patent: CN106565434,2017,A .Location in patent: Paragraph 0128-0131

88
ethyl 1-bromo-3-methyl-4-oxo-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate [ No CAS ]
[ 108238-09-1 ]
ethyl 3-methyl-4-oxo-1-(2-phenoxyphenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2225 - 2233

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H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 108238-09-1 ] {[proInfo.proName]}

Quality Control of [ 108238-09-1 ]

Related Doc. of [ 108238-09-1 ]

Product Details of [ 108238-09-1 ]

Calculated chemistry of [ 108238-09-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 108238-09-1 ]

Application In Synthesis of [ 108238-09-1 ]

[ 108238-09-1 ] Synthesis Path-Upstream 1~8

[ 108238-09-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 108238-09-1 ]

Organoboron

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 108238-09-1 ]