[ CAS No. 957065-99-5 ] {[proInfo.proName]}

Name: 957065-99-5|Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate|97%
Brand: Ambeed
SKU: A564950
Price: 6.0 USD
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Quality Control of [ 957065-99-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 957065-99-5 ]

Product Details of [ 957065-99-5 ]

CAS No. :	957065-99-5	MDL No. :	MFCD08063051
Formula :	C₁₃H₁₈BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IXKFGVRURWXXKX-UHFFFAOYSA-N
M.W :	263.10	Pubchem ID :	46738663
Synonyms :

Calculated chemistry of [ 957065-99-5 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	71.99
TPSA :	57.65 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.02
Log Po/w (WLOGP) :	1.17
Log Po/w (MLOGP) :	0.45
Log Po/w (SILICOS-IT) :	1.23
Consensus Log Po/w :	0.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.78
Solubility :	0.437 mg/ml ; 0.00166 mol/l
Class :	Soluble
Log S (Ali) :	-2.86
Solubility :	0.365 mg/ml ; 0.00139 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.7
Solubility :	0.0521 mg/ml ; 0.000198 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.99

Safety of [ 957065-99-5 ]

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 [ 957065-99-5 ]

* 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 [ 957065-99-5 ]
Downstream synthetic route of [ 957065-99-5 ]

[ 957065-99-5 ] Synthesis Path-Upstream 1~2

1
[ 29682-15-3 ]
[ 73183-34-3 ]
[ 957065-99-5 ]

Reference： [1] Patent: WO2009/156966, 2009, A1, . Location in patent: Page/Page column 38-39
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 1011 - 1020

2
[ 624-28-2 ]
[ 957065-99-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 1011 - 1020

[ 957065-99-5 ] Synthesis Path-Downstream 1~18

1
[ 1155878-19-5 ]
[ 957065-99-5 ]
[ 1155877-30-7 ]

Yield	Reaction Conditions	Operation in experiment
15%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 1h;Product distribution / selectivity;	5-(3'-Chloro-6-methoxy-biphenyl-3-ylmethyl)-pyridine-2-carboxylic acid methyl ester Into a 250 mL round bottom flask was added 5-Bromomethyl-3'-chloro-2-methoxy-biphenyl (Int-51, prepared in a similar manner as Int-20, 4.89 g, 15.69 mmol), 5-(1,5-Dimethyl-2,4-dioxa-3-bora-bicyclo[3.1.0]hex-3-yl)-pyridine-2-carboxylic acid methyl ester (4.52 g, 17.26 mmol), toluene (120 mL), EtOH (20 mL), water (20 mL), and K3PO4 (6.66 g, 31.38 mmol). The suspension was degassed with N2 for 15 minutes and then Pd(PPh3)4 (1.81 g, 1.57 mmol) was added and the reaction was stirred at 80 C. for 1 hour. The layers were separated and the aqueous was extracted with 50 mL EtOAc. The organics were combined and washed with 50 mL brine, dried over Na2SO4, and concentrated. The residue was purified by flash column chromatography eluding with 10% Acetone/Hexanes to afford the title compound (0.89 g, 15%) as a light-yellow oil.

Reference： [1]Patent: US2009/136473,2009,A1 .Location in patent: Page/Page column 52

2
[ 957065-99-5 ]
[ 1155877-73-8 ]
[ 1155876-82-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate;bis(eta3-allyl-mu-chloropalladium(II)); 1,5-bis-(diphenylphosphino)pentane; In N,N-dimethyl-formamide; at 65℃; for 50h;	A-020 Synthesis of 5-(3'-Acetyl-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridine-2-carboxylic acid methyl ester A suspension of Int-7 (500 mg, 1.50 mmol), 2-methylcarboxypyridine-5-boronic acid pinocol ester (435 mg, 1.65 mmol), and potassium carbonate (624 mg, 4.51 mmol) in dimethylformamide (3.5 mL) was degassed under a nitrogen stream for 15 min. To this solution was added bis(diphenylphosphino)pentate (199 mg, 0.451 mmol) and allylpalladiumchloride dimer (82.7 mg, 0.226 mmol). The reaction was heated to 65 C. for 50 h. The reaction was diluted with ethyl acetate (50 mL) and filtered through celite. To the filtrate was added water (50 mL), and the layers separated. The aqueous wash was extracted with ethyl acetate (2*50 mL), and all three organic extracts combined and washed with brine (100 mL). The organic solution was dried over magnesium sulfate, filtered, and the solvent removed under vacuum. The residue was purified by flash silica gel column chromatography (5% acetone in dichloromethane) and triturated in diethyl ether (15 mL), filtered, and washed with diethyl ether (5 mL) to give A-020 (190.6 mg, 32% yield) as a white powder. 1H NMR (400 MHz CDCl3) d: 8.656 (d, J=2.00 Hz, 1H), 8.062 (d, J=8.00 Hz, 1H), 7.973-7.940 (m, 2H), 7.665 (dd, J=8.20 Hz, 2.20 Hz, 1H), 7.574 (dd, J=7.60 Hz, 1.60 Hz, H), 7.518 (t, J=7.60 Hz, 1H), 7.125 (t, J=8.60 Hz, 1H), 6.747 (d, J=8.80 Hz, 1H), 4.053 (s, 2H), 3.996 (s, 3H), 3.765 (s, 3H), 2.618 (s, 3H). LCMS=100.0% purity. MS (APCI+)=394.1 (M+1).

Reference： [1]Patent: US2009/136473,2009,A1 .Location in patent: Page/Page column 27

3
[ 957065-99-5 ]
[ 1155878-05-9 ]
[ 1155877-25-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate;bis(eta3-allyl-mu-chloropalladium(II)); 1,5-bis-(diphenylphosphino)pentane; In N,N-dimethyl-formamide; at 85℃; for 4h;	A-075 Synthesis of 5-(3'-Chloro-6-difluoromethoxy-biphenyl-3-ylmethyl)-pyridine-2-carboxylic acid methyl ester In a 40 mL vial equipped with a stir bar was placed Int-45 (700 mg, 2.04 mmol), <strong>[957065-99-5]5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carboxylic acid methyl ester</strong> (590 mg, 2.24 mmol), potassium carbonate (846 mg, 6.12 mmol), 1,5-bis(diphenylphosphino)pentane (270 mg, 0.612 mmol) and DMF (10 mL). The reaction mixture was degassed for 15 minutes by bubbling nitrogen and then allylpalladium(II) chloride dimer (112 mg, 0.306 mmol) was added. The reaction mixture was heated to 85 C. for 4 hours. To the reaction mixture was added water (40 mL) and ethyl acetate (40 mL) and the mixture was filtered through Celite. The layers of the filtrate were separated and the aqueous portion was extracted with ethyl acetate (40 mL). The organic portions were combined, washed with brine (40 mL), dried (MgSO4) and concentrated. The crude material was purified by a 50 gram silica gel SNAP cartridge (Biotage SP4 Flash Chromatography instrument) utilizing gradient elution of 12-100% ethyl acetate/hexanes to produce 458 mg A-075 as a viscous yellow solid in 56% yield. 1H NMR (400 MHz, DMSO-d6) delta 3.86 (s, 3H), 4.12 (s, 2H), 7.13 (t, J=74 Hz, 1H), 7.25 (d, J=8 Hz, 1H), 7.37 (dd, J=8, 2 Hz, 1H), 7.57 (dt, J=7, 2 Hz, 1H), 7.44-7.52 (m, 4H), 7.88 (dd, J=8, 2 Hz, 1H), 7.99 (d, J=8 Hz, 1H), 8.71 (s, 1H). MS (APCI+): 404.5 (M+1) LC/MS: 98%

Reference： [1]Patent: US2009/136473,2009,A1 .Location in patent: Page/Page column 49

4
[ 957065-99-5 ]
[ 1160789-85-4 ]
[ 1160790-07-7 ]

Yield	Reaction Conditions	Operation in experiment
6%		A solution of 2-methoxycarbonyl-5-pyridineboronic acid, pinacol ester (0.20 g, 0.75 mmol), 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea (0.15 g, 0.50 mmol) and K3PO4 (0.21 g, 1.0 mmol) in DMF-H2O (7.0 ml_, 5:2) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)-palladiurn(ll) (0.03 g, 0.05 mmol) was then added to the reaction mixture followed by degassing with nitrogen for another 15 min. The resulting reaction mixture was then heated to 8O0C for 16 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to room temperature and poured onto ice-cold water followed by extraction with EtOAc (2 x 50 ml_). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was then purified over silica gel (100-200 M, 100% EtOAc) to obtain the desired product (0.01 g, 6%). 1H-NMR (400 MHz, DMSO-d6): delta 1.09 (t, J= 7.20 Hz, 3H), 3.19 (m, 2H), 3.91 (s, 3H), 6.75 (br s, 1 H), 7.66 (d, J= 9.60 Hz, 1 H), 8.05 (m, 2H), 8.14 (d, J= 8.40 Hz, 1H), 8.36 (m, 1 H), 9.11 (s, 1 H) and 10.78 (br s, 1 H). MS: 357.15 (M+H)+. Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 266 nm): 92.29% (Rt = 4.99 min).

Reference： [1]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 30

5
[ 29682-15-3 ]
[ 73183-34-3 ]
[ 957065-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 20 - 90℃;Inert atmosphere;	Step 4: Synthesis of methyl 5-(4,4,5,5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)pyridine-2- carboxylate:; To a solution of <strong>[29682-15-3]5-bromo-pyridine-2-carboxylic acid methyl ester</strong> (0.5 g, 2.3 mmol) in 1,4 dioxane (25 mL) were added bispinacolatodiborane (1.05 g, 4.1 mmol), potassium acetate <n="40"/>(1.13 g, 11.5 mmol) and Pd (dppf)Cl2 (0.28 g, 0.34 mmol) under argon at room temperature. The mixture was heated at 80-900C for about 6 hours. It was cooled to room temperature, concentrated under reduced pressure and then purified through filtering column using sintered funnel full of 230-400 mesh size silica gel. It was eluted with 50% ethylacetate in hexane and concentrated to afford title compound (0.23 g). MS m/e .264.27. (MH+)
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; water; at 110℃; for 0.25h;Sealed tube; Microwave irradiation;	General procedure: A mixture of 2a or 2b (1 g, 1 equiv.), bis(-pinacolato)diboron (1.2 equiv.), [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane(10 mol %), potassium acetate (2 equiv.), 1,4-dioxane (15 ml) andwater (7.5 ml) was sealed in a 20 ml microwave reaction vial(Biotage). The vial was irradiated in a microwave apparatus at110 C, high absorption for 15 min. The reaction mixturewas cooledto room temperature (afforded crude 3a or 3b) and used to the nextstep without purification. An appropriate alkyl halide (0.95 equiv.),cesium carbonate (2.0 equiv) and water (4 ml) were added directlyto the reaction mixture. The vial was sealed and irradiated in amicrowave apparatus at 110 C, normal absorption for 30-90 min.After cooling to room temperature, water (100 ml) was added andthe mixture was extracted with ethyl acetate (4 x 100 ml). Theorganic layer was washed with brine (200 ml), dried with anhydrousNa2SO4(s) and concentrated. The residue was purified bysilica-gel flash column chromatography (eluent: ethyl acetate/heptane = 1:1) to obtain the esters 4a and 4j-m.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 3h;Inert atmosphere;	The compound 156a (500 mg, 2.31 mmol) was dissolved in 1,4-dioxane (20 mL), and the compound 156b (705.3 mg, 2.78 mmol), KOAc (453.6 mg, 4.63 mmol) and PdCl2 ( dppf) (169.4 mg, 0.23 mmol), replaced with nitrogen three times, and then the reaction solution was stirred at 90 C for 3 hours. Cooled to room temperature, filtered and concentrated, the concentrate was used directly in the next reaction feed.

Reference： [1]Patent: WO2009/156966,2009,A1 .Location in patent: Page/Page column 38-39
[2]European Journal of Medicinal Chemistry,2017,vol. 126,p. 1011 - 1020
[3]Patent: CN110627775,2019,A .Location in patent: Paragraph 0379-0380; 0381-0382
[4]Medicinal Chemistry Research,2020

6
[ 957065-99-5 ]
[ 1204129-87-2 ]
[ 1204130-26-6 ]

Yield	Reaction Conditions	Operation in experiment
		A Smith-Process vial is charged with Intermediate AIc (206 mg,0.5 mmol), <strong>[957065-99-5]methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate</strong> (158 mg, 0.6 mmol), dichloro[l,r-bis(diphenylphosphino)ferrocene]palladium(II) (18 mg, 5 mol%), and dry dioxane (2.5 rnL). To the solution is added IM aqueous Cs2CO3 (1.7 rnL, 1.7 mmol), and the biphasic mixture is subjected to microwave irradiation (13OC, 30 min). Brine (30 mL) is added, the precipitate is filtered, washed with H2O (2 x 1 mL), Et2O (3 x 10 mL) and dried in vacuo to afford 5-(4-((l-(5-ethylpyrimidin-2-yl)piperidin-4- yl)methoxy)-3,5-difluorophenyl)picolinic acid sodium salt Ila as a brown solid. The crude compound is used in the next step without further purification: MS calcd. for [M+H]+ C24H25F2N4O3: 455.2, found: 455.2.

Reference： [1]Patent: WO2010/6191,2010,A1 .Location in patent: Page/Page column 70-71

7
[ 957065-99-5 ]
4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine [ No CAS ]
[ 76-05-1 ]
5-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-pyridine-2-carboxylic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. 5-{2-[2-amwo-6~(4-methylpiotaperaziotan-l-yl)pyrimidin-4-y1]-3-methyl-l,2,3,4-tetrahydroisoquinolm- 7-yl}pyridine-2-carboxyhcacidH2N A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(lH)-yl)-6-(4-methylpiperazin-l - yl)pyrimidin-2-amine (100 mg, 0.2 mmol) (Peak 1, Example 49, Step 7), methyl 5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate (75.6 mg, 0.287 mmol, Frontier. Cat. No. M2012 ), [1,1'- bis(diphenylphosphino)fertauocene] dichloropalladium(ll) complex with dichloromethane (1 :1) (1 1.7 mg, 0.0144 mmol), and potassium phosphate ( 152 6 mg, 0.7188 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was degassed with nitrogen and heated at 120 0C overnight. The reaction mixture was cooled to r.t. and filtered. The filtrate was concentrated to dryness. The residue was dissolved in MeOH and purified by RP-HPLC (pH = 2) to afford the desired compound as TFA salt. LCMS (M+H)+: m/z = 460.3.; Step 1: 5-{2-[2-ammo-6-(4-methylpiperazm-l-yl)pyrimidin-4-yl]-3-methyl-l,2, 3, 4-tetrahydroisoquinolin- 7-yl}pyridine-2-carbox)>licacidH2N A mixture of 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(lH)-yl)-6-(4-methylpiperazin-l- yl)pyrimidin-2-amine (100 mg, 0.2 mmol) (Peak 2, Example 49, Step 7), methyl 5-(4,4,5,5-tetramethyl- 1.3,2-dioxaborolan-2-yI)pyridine-2-carboxylate (75.6 mg, 0.287 mmol, Frontier, Cat. No. M2012 ), [L l'- bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with dichloromethane (1 : 1) (1 1.7 mg, 0.0144 mmol), and potassium phosphate ( 152.6 mg, 0.7188 mmol) in l,4-dioxane (5 niL) and water (l mL) was degassed with nitrogen and heated at 120 0C overnight. The reaction mixture was cooled to r.t. and filtered. The filtrate was concentrated to dryness. The residue was dissolved in MeOH and purified by RP-HPLC (pH = 2) to afford the desired compound as TFA salt. LCMS (M+H)+: m/z = 460.3.

Reference： [1]Patent: WO2010/75270,2010,A1 .Location in patent: Page/Page column 101-103

8
[ 957065-99-5 ]
[ 1227165-17-4 ]
[ 1227243-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;bis(eta3-allyl-mu-chloropalladium(II)); 1,5-bis-(diphenylphosphino)pentane; In N,N-dimethyl-formamide; at 90℃; for 2h;	A reaction mixture of compound 16 (200 mg crude, 0.55 mmol), 2-(methylcarboxy) pyridine-5-boronic acid pinacol este (145 mg, 0.55 mmol), l,5-bis(diphenylphosphino) pentane (73 mg, 0.165 mmole), allylpalladium chloride dimer (30 mg, 0.082 mmol), K2CO3 (228 mg, 1.65 mmole) in DMF (3 ml)) was stirred at 90 0C for 2 hours and then cooled to room temperature. Water was added and the aqueous portion was extracted with ethyl acetate (3 x 8 ml), the organic portions were combined, washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography utilizing MeOH/DCM as the eluent to give 72 mg of D-18 in 33 % yield for two step. To a solution of D-18 (11 mg) in DCM (3 ml), was added HCl in Et2O (2N, 0.1 ml), solid was washed with ether to give 11 mg of D-18 HCl salt as solid. 1H-NMR (400 MHz, CD3OD): 2.52 (3H, s), 4.01 (2H, s), 4.39 (2H, s), 7.57 - 7.63 (3H, m), 7.72 (IH, m), 7.84 (IH, m), 8.00 (IH, m), 8.20 (IH, m), 8.26 (IH, d, J=8 Hz), 8.69, IH, m), 8.78 (IH, m). MS(APCI+): 392.0 (M+ 1). LC-MS: 98 %.
	With potassium carbonate;bis(eta3-allyl-mu-chloropalladium(II)); 1,5-bis-(diphenylphosphino)pentane; In N,N-dimethyl-formamide; at 90℃; for 2h;	Synthesis of 5-[8-(3-Chloro-phenyl)-2-methyl-imidazo[l,2-a]pyridin-6- ylmethyl]-pyridine-2-carboxylic acid methyl ester (D-18): A reaction mixture of compound 16 (200 mg crude, 0.55 mmol), 2-(methylcarboxy) pyridine-5-boronic acid pinacol este (145 mg, 0.55 mmol), l,5-bis(diphenylphosphino) pentane (73 mg, 0.165 mmole), allylpalladium chloride dimer (30 mg, 0.082 mmol), K2CO3 (228 mg, 1.65 mmole) in DMF (3 ml)) was stirred at 90 0C for 2 hours and then cooled to room temperature. Water was added and the aqueous portion was extracted with ethyl acetate (3 x 8 ml), the organic portions were combined, washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography utilizing MeOH/DCM as the eluent to give 72 mg of D-18 in 33 % yield for two step. To a solution of D-18 (11 mg) in DCM (3 ml), was added HCl in Et20 (2N, 0.1 ml), solid was washed with ether to give 11 mg of D-18 HCl salt as solid. 1H-NMR (400 MHz, CD3OD): 2.52 (3H, s), 4.01 (2H, s), 4.39 (2H, s), 7.57 - 7.63 (3H, m), 7.72 (IH, m), 7.84 (IH, m), 8.00 (IH, m), 8.20 (IH, m), 8.26 (IH, d, J=8 Hz), 8.69, IH, m), 8.78 (IH, m). MS(APCI+): 392.0 (M+ 1). LC-MS: 98 %.

Reference： [1]Patent: WO2010/59838,2010,A2 .Location in patent: Page/Page column 113-114
[2]Patent: WO2010/59836,2010,A1 .Location in patent: Page/Page column 54-55

9
[ 957065-99-5 ]
[ 1254171-04-4 ]
[ 1254171-44-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 16h;Inert atmosphere;	Synthesis of 2-(2-chloro-6-fluorophenyl)-5-(6-(3-isopropyl-l,2,4-oxadiazol-5-yl)pyridin-3- vP- lH-imidazole-4-carbonitrile (EX-116)[000296] To a solution of 5-bromo-2-(2-chloro-6-fluorophenyl)-lH-imidazole-4- carbonitrile (1-10) (2.5 mmol) and methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)picolinate (R-45) (1.67 mmol) in a 2 : 1 : 1 toluene : ethanol : water solution was added Pd(PPh3)4 (0.17 mmol) and K2CO3 (3.34 mmol). The reaction mixture was degassed with nitrogen, and then heated at 100 0C for 16 hours. After cooling to room temperature the crude product was purified by preparative HPLC (MeCN gradient 5 -70%) to yield 5-(2-(2- chloro-6-fluorophenyl)-4-cyano-lH-imidazol-5-yl)picolinic acid (1-40) as a white solid. MS (m/z) (M+ 1)+: 343.1.[000297] To a solution of S-^-^-chloro-beta-fluorophenylM-cyano-lH-imidazol-S- yl)picolinic acid (1-40) (0.29 mmol) in DMF (5 rnL) was added iV-hydroxybenzotriazole (0.44 mmol) followed by l-ethyl-3-(3'-dimethylaminopropyl)carbodiimide (0.44 mmol) and (Z)-N'-hydroxyisobutyrimidamide (R- 34) (0.44 mmol). The resulting solution was stirred at room temperature for 2 hours and then heated to 85 0C for 4 hours. After cooling to room temperature the reaction mixture was purified by preparative EtaPLC (MeCN gradient 10- 90%). 2-(2-Chloro-6-fluorophenyl)-5-(6-(3-isopropyl-l,2,4-oxadiazol-5-yl)pyridin-3-yl)- lH-imidazole-4-carbonitrile (EX-116) was obtained as a white solid. MS (m/z) (M+l)+: 409.1.

Reference： [1]Patent: WO2010/127152,2010,A2 .Location in patent: Page/Page column 113-114

10
[ 957065-99-5 ]
[ 139585-70-9 ]
[ 1206621-19-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 105℃; for 0.25h;Microwave irradiation;	To a microwave vial was added methyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2- pyridinecarboxylate (2 g, 7.60 mmol), 6-bromo-3-pyridinecarbonitrile (2.09 g, 1 1.40 mmol), PdCI2(dppf)-CH2CI2 adduct (0.62 g, 0.760 mmol), NaHCO3 (1.277 g, 15.20 mmol), 1 ,4- dioxane (8 ml) and water (2 ml). The mixture was microwaved for 15 min at 105 0C. The resulting dark solution was diluted with water and CH2CI2. The aqueous layer was extracted three times with CH2CI2. The CH2CI2 extracts were passed over a phase separator, concentrated and purified on a Biotage SP4 with a 65i column at a flow rate of 65 ml/min, 0.1% TFA eluting with 2CV water, the 0-100% ACN/Water over 10CV. The fractions containing the product were combined and diluted with CH2CI2 and sat. NaHCO3. The layers were separated and the aqueous layer was extracted twice with CH2CI2, then the combined organic extracts were dried and concentrated to afford the desired product (1.0 g, 1.75 mmol) as an off white solid. LCMS (m/z): 262.0 (M+Na).

Reference： [1]Patent: WO2010/11914,2010,A1 .Location in patent: Page/Page column 54

11
[ 957065-99-5 ]
[ 1257553-04-0 ]
[ 1257547-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 20℃; for 43h;Inert atmosphere;	A mixture of 8-bromo-1-(1,3-dimethyl-1 H-pyrazol-4-yf)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 39 mg, 0 105 mmol), 2-methylcarboxypyndine-5-boronic acid pinacol ester (Aalen Chemical, Nanjing, China, 49 mg, 0 186 mmol), potassium fluoride (22 mg, 0 379 mmol), Pd2(dba)3 (7.7 mg, 0 0085 mmol) and tri-t-butylphosphonium tetrafluoroborate (4.9 mg, 0 017 mmol) in dioxane (0.6 m.) was stirred under argon in a sealed microwave tube at rt for 20 h. The reaction was not completed Therefore, again Pd2(dba)3 (7.7 mg 0 0085 mmoi) and tri-t-butylphoUSDphonium tetrafluoroborate (4.9 mg, 0 017 mmol) and 2-methylcarboxypyrid)ne-5-boronic acid pinacol ester (Combi-Blocks San Diego, USA, 15 mg, 0 186 mmol) were added, the mixture was flushed with argon and stirred at rt for further 23 h. The RM was diluted with EtOAc The organic layer was washed with brine, dried over Na2SO4 filtered and evaporated The residue was dissolved in MeOH and purified directly by Prep HPLC (H2O (0 1% TFA)/CH3CN 95 5 to 60 30) The fractions containing products were collected together and basified with NaHCO3 (0.3 g), before being concentrated The resulting suspension was filtered and the cake was washed with water, before being dried under high vacuum to give the title compound as a white solid (HPUC t?2 45 min (Method A), M+H = 429 MS-ES, 1H-NMR (d6-DMSO, 400 MHz) 8 99 (s, 1H) 8.83- 8 78 (m, 1 H)1 8 20-8 12 (m, 3H), 8.11-8 06 (m 1H), 8 05-7 98 (m, 1H)1 7.69-7.62 (m, 1H),3 92 (s, 3H), 3.90 (s, 3H), 3 58 (s, 3H), 1 96 (s, 3H)).

Reference： [1]Patent: WO2010/139731,2010,A1 .Location in patent: Page/Page column 211

12
[ 957065-99-5 ]
[ 1033244-97-1 ]
[ 1330075-51-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4550 - 4555

13
[ 957065-99-5 ]
[ 59142-68-6 ]
[ 1415130-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,4-dioxane; water at 65℃; for 1.5h;	53.A 2-bromo-4-fluorobenzaldehyde (800 mg, 3.9 mmol), methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (1.2 g, 4.7 mmol), Pd(dppf)Cl2 (433 mg, 0.6 mmol), and K2CO3 (1.1 g, 7.9 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 65° C. After 1.5 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/302610, 2012, A1 Location in patent: Page/Page column 47

14
[ 957065-99-5 ]
[ 493024-39-8 ]
methyl 5-(3-chloro-5-fluorobenzyl)picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; acetonitrile at 80℃; for 3h; Inert atmosphere;	79.1 Step 1 : Preparation of methyl 5-(3-chloro-5-fluorobenzyl)picolinate To a solution of methyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinate (1 .0 g, 3.8 mmol) in acetonitrile (20 ml_) and water (5 ml_) at room temperature was added potassium carbonate (1 .05 g, 7.6 mmol), 1 ,1 '-b/s(diphenylphosphino)ferrocene palladium(ll)dichloride (0.310 g, 0.38 mmol) and 1 -(bromomethyl)-3-chloro-5-fluorobenzene (0.850 g, 3.8 mmol) under nitrogen. The reaction mixture was stirred at 80 °C for 3 h. The reaction solution was cooled to room temperature and diluted with water (200 ml_) The aqueous layer was extracted with ethyl acetate (100 ml_ c 3). The combined organic layers were washed with brine (1 00 ml_), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 3/1 ) to give methyl 5-(3-chloro-5-fluorobenzyl)picolinate (0.550 g, 1 .97 mmol, 52%) as a yellow solid. LCMS (ESI) m/z: 280.0 [M+H]+.
52%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; acetonitrile at 80℃; for 3h; Inert atmosphere;	79.1 Step 1 : Preparation of methyl 5-(3-chloro-5-fluorobenzyl)picolinate To a solution of methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (1.0 g, 3.8 mmol) in acetonitrile (20 ml_) and water (5 ml_) at room temperature was added potassium carbonate (1.05 g, 7.6 mmol), 1,1 '-Jb/s(diphenylphosphino)ferrocene palladium(ll)dichloride (0.310 g, 0.38 mmol) and 1 -(bromomethyl)-3-chloro-5-fluorobenzene (0.850 g, 3.8 mmol) under nitrogen. The reaction mixture was stirred at 80 °C for 3 h. The reaction solution was cooled to room temperature and diluted with water (200 ml_) The aqueous layer was extracted with ethyl acetate (100 ml_ c 3). The combined organic layers were washed with brine (100 ml_), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 3/1) to give methyl 5-(3-chloro-5-fluorobenzyl)picolinate (0.550 g, 1.97 mmol, 52%) as a yellow solid. LCMS (ESI) m/z: 280.0 [M+H]+.

Reference： [1]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2019/183587, 2019, A1 Location in patent: Page/Page column 187
[2]Current Patent Assignee: YUMANITY THERAPEUTICS INC; EUMANNICH TREAT - WO2020/198026, 2020, A1 Location in patent: Page/Page column 193-194

15
[ 957065-99-5 ]
[ 85118-01-0 ]
methyl 5-(3,4-difluorobenzyl)picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; acetonitrile at 80℃; for 3h; Inert atmosphere;	87.1 Step 1 : Preparation of methyl 5-(3,4-difluorobenzyl)picolinate To a solution of methyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinate (1 .0 g, 3.8 mmol) in acetonitrile (20 ml_) and water (5 ml_) at room temperature was added potassium carbonate (1 .04 g, 7.6 mmol), 1 ,1 '-b/s(diphenylphosphino)ferrocene palladium(ll)dichloride (0.310 g, 0.38 mmol) and 4-(bromomethyl)-1 ,2-difluorobenzene (0.787 g, 3.8 mmol) under nitrogen. The reaction mixture was stirred at 80 °C for 3 h. The reaction solution was cooled to room temperature and diluted with water (200 ml_). The aqueous layer was extracted with ethyl acetate (80 ml_ c 3). The combined organic layers were washed with brine (1 00 ml_), dried over anhydrous sodium sulfate, filtered and concentrated. The crude sample was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 3/1 ) to give methyl 5-(3,4-difluorobenzyl)picolinate (0.610 g, 2.31 mmol, 61 %) as a yellow solid. LCMS (ESI) m/z: 264.1 [M+H]+.
61%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; acetonitrile at 80℃; for 3h; Inert atmosphere;	87.1 Step 1 : Preparation of methyl 5-(3,4-difluorobenzyl)picolinate To a solution of methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (1.0 g, 3.8 mmol) in acetonitrile (20 ml_) and water (5 ml_) at room temperature was added potassium carbonate (1.04 g, 7.6 mmol), 1,T-Jb/s(diphenylphosphino)ferrocene palladium(ll)dichloride (0.310 g, 0.38 mmol) and 4-(bromomethyl)-1,2-difluorobenzene (0.787 g, 3.8 mmol) under nitrogen. The reaction mixture was stirred at 80 °C for 3 h. The reaction solution was cooled to room temperature and diluted with water (200 ml_). The aqueous layer was extracted with ethyl acetate (80 ml_ c 3). The combined organic layers were washed with brine (100 ml_), dried over anhydrous sodium sulfate, filtered and concentrated. The crude sample was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 3/1) to give methyl 5-(3,4-difluorobenzyl)picolinate (0.610 g, 2.31 mmol, 61 %) as a yellow solid. LCMS (ESI) m/z: 264.1 [M+H]+.

Reference： [1]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2019/183587, 2019, A1 Location in patent: Page/Page column 195-196
[2]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2020/198026, 2020, A1 Location in patent: Page/Page column 202

16
[ 42881-66-3 ]
[ 957065-99-5 ]
methyl 5-(6-methoxyquinolin-4-yl)picolinate [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2020,vol. 29,p. 1689 - 1696

17
[ 957065-99-5 ]
[ 61655-69-4 ]
methyl 5-[6-(trifluoromethyl)pyrazin-2-yl]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 1h;	212 Synthesis of 212.1. Synthesis of 212.1.

Reference： [1]Current Patent Assignee: NIMBUS CLOTHO - WO2022/87634, 2022, A1 Location in patent: Paragraph 001003

18
[ 1111638-05-1 ]
[ 957065-99-5 ]
methyl 5-[2-methylimidazo[1,2-a]pyrimidin-6-yl]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 2h; Inert atmosphere;	26 Synthesis of 26.1 Synthesis of 26.1

Reference： [1]Current Patent Assignee: NIMBUS CLOTHO - WO2022/87634, 2022, A1 Location in patent: Paragraph 00441

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H221	Flammable gas
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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
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H332	Harmful if inhaled
H333	May be harmful if inhaled
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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. 957065-99-5 ] {[proInfo.proName]}

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[ 957065-99-5 ] Synthesis Path-Upstream 1~2

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Organoboron

Esters

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Pyridines

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