[ CAS No. 4467-07-6 ] {[proInfo.proName]}

Name: 4467-07-6|3-(Pyridin-2-yl)benzoic acid|98%
Brand: Ambeed
SKU: A153785
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Quality Control of [ 4467-07-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4467-07-6 ]

Product Details of [ 4467-07-6 ]

CAS No. :	4467-07-6	MDL No. :	MFCD05864807
Formula :	C₁₂H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IRXFQXMHMRTLIR-UHFFFAOYSA-N
M.W :	199.21	Pubchem ID :	5152592
Synonyms :

Calculated chemistry of [ 4467-07-6 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.63
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.16
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	1.61
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	2.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.9
Solubility :	0.253 mg/ml ; 0.00127 mol/l
Class :	Soluble
Log S (Ali) :	-2.85
Solubility :	0.284 mg/ml ; 0.00142 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.92
Solubility :	0.0239 mg/ml ; 0.00012 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 4467-07-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4467-07-6 ]

* 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 [ 4467-07-6 ]
Downstream synthetic route of [ 4467-07-6 ]

[ 4467-07-6 ] Synthesis Path-Upstream 1~10

1
[ 109-04-6 ]
[ 25487-66-5 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In water; acetonitrile at 100℃; for 24 h; Inert atmosphere	Example 161 A3-(pyridin-2-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II)chloride (400 mg, 0.37 mmol) was added. The mixture was degassed and purged withed nitrogen. The mixture was stirred at 100° C. for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.69 g of white solid of 3-(pyridin-2-yl)benzoic acid. Yield: 85percent. LC-MS (ESI) m/z: 200 (M+1)⁺.

Reference： [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 75

2
[ 98061-20-2 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With water; sodium hydroxide In methanol at 20℃; for 3 h;	[00336] To a solution of methyl 3-(pyridin-2-yl)benzoate (400 mg, 1.88 mmol) in MeOH (3 mL) was added aqueous of NaOH (1 mL, 40 molpercent). The reaction mixture was stirred at room temperature for 3 h and concentrated. The crude residue was dissolved in water and the pH was adjusted to 5-6 with 2N of HCl. The solution was extracted with ethyl acetate, brine, dried over sodium sulfate, filtered and concentrated. (350 mg, yield 93percent) MS (ESI+) e/z: 200.1 [M+l]+.

Reference： [1] Patent: WO2014/100734, 2014, A1, . Location in patent: Paragraph 00336
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 162 - 166

3
[ 1432795-28-2 ]
[ 585-76-2 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 95℃; Inert atmosphere	General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 634 - 648

4
[ 109-04-6 ]
[ 269409-73-6 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In water; N,N-dimethyl-formamide at 110℃; Inert atmosphere	To a degassed souton of DMF:H20 (10:1 raUo) (0.3 M), under an atmosphere of nitrogen, was added the pnaco ester (1 mmo), 2-bromopyrdne or 2-choropyrmdne (1 .5 eq.), and Cs2CO3 (4.4 eq.). The whoe mxture was degassed once agan and then Pd(PPh3)4 (5mopercent) was added. The resutng souton was heated to 110°C overnght. The sovent was removed in vacuo to give a dark gummy residue, which was taken up nto EtOAc and H20, then acdfied with 2 M HC to pH 2. The organic ayer was separated and the aqueous ayer was further extracted with EtOAc (2x). The combined organic ayers were dried over MgSO4 and concentrated in vacuo to gve a back ofly residue. The residue was dry oaded ontosWca ge in vacuo then purfied by flash coumn chromatography, eutng with 10-30percent EtOAc/petroeum benzne and 1percent acetic acid to afford the tWe compound.The foHowng compounds were made by Suzuk CoupUng F:P1B1Off white soUd (75percent yed). 1H NMR (400 MHz,DMSO) 6 8.71 8.68 (m, 1 H), 8.67 (s, 1 H), 8.29 (d,J = 7.8 Hz, 1 H), 8.01 (t, J = 8.4 Hz, 2H), 7.91 (td, J =7.8, 1.8 Hz, 1 H), 7.61 (t, J = 7.7 Hz, 1 H), 7.42 7.37(m, 1H). LCMS B rt3.17, m/z200.1 [M + H].

Reference： [1] Patent: WO2016/198507, 2016, A1, . Location in patent: Page/Page column 40; 50

5
[ 109-04-6 ]
[ 4467-07-6 ]

Reference： [1] Inorganic Chemistry Communications, 2013, vol. 32, p. 78 - 81
[2] Patent: WO2014/100734, 2014, A1,
[3] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 162 - 166

6
[ 4373-61-9 ]
[ 4467-07-6 ]

Reference： [1] Inorganic Chemistry Communications, 2013, vol. 32, p. 78 - 81
[2] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516

7
[ 17933-03-8 ]
[ 4467-07-6 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516

8
[ 99769-19-4 ]
[ 4467-07-6 ]

Reference： [1] Patent: WO2014/100734, 2014, A1,
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 162 - 166

9
[ 591-17-3 ]
[ 4467-07-6 ]

Reference： [1] Inorganic Chemistry Communications, 2013, vol. 32, p. 78 - 81

10
[ 585-76-2 ]
[ 4467-07-6 ]

Reference： [1] Patent: WO2016/198507, 2016, A1,

[ 4467-07-6 ] Synthesis Path-Downstream 1~44

2
[ 109-04-6 ]
[ 25487-66-5 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 100℃; for 24.0h;Inert atmosphere;	Example 161 A3-(pyridin-2-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II)chloride (400 mg, 0.37 mmol) was added. The mixture was degassed and purged withed nitrogen. The mixture was stirred at 100 C. for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.69 g of white solid of 3-(pyridin-2-yl)benzoic acid. Yield: 85%. LC-MS (ESI) m/z: 200 (M+1)+.

Reference： [1]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 75

3
[ 4467-07-6 ]
3-(pyridin-2-yl)benzoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;Reflux;	Example 161 Bmethyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate; Thionyl chloride (10 mL) was added to <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> (1.69 g, 8.5 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum to give 3-(pyridin-2-yl)benzoyl chloride. 1.66 g of crude product was obtained. To a solution of methyl 3-amino-2-hydroxybenzoate (0.84 g, 5 mmol) and pyridine (790 mg, 10 mmol) in toluene (50 mL) were added crude 3-(pyridin-2-yl)benzoyl chloride (1.6 g, 7.37 mmol) portion-wise at 0 C. and then stirred at 70 C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL×4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain yellow solid of methyl 2-hydroxy-3-(3-(pyridin-2-yl)benzamido)benzoate (1.48 g, yield 85%). LC-MS (ESI) m/z: 349 (M+1)+.

Reference： [1]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 75

4
ammonium hexafluorophosphate [ No CAS ]
[ 345911-20-8 ]
[ 7732-18-5 ]
[ 4467-07-6 ]
[Ru(2,2'-bipyridine)2(3-(2-pyridinyl)benzoic acid(-H))]PF₆*0.5water [ No CAS ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 9631 - 9643

5
ammonium hexafluorophosphate [ No CAS ]
[ 15746-57-3 ]
[ 4467-07-6 ]
[Ru(bpy)2(ppy)]PF₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		To a flask containing 95 mg (0.48 mmol) of <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> and 20 mg (0.50 mmol) of NaOH was added 30 mL of degassed aqueous methanol solution (Fi20:MeOH 1 :5 v/v). The reagents were stirred until all components were dissolved and then transferred to a flask containing 188 mg (0.362 mmol) of Ru(bpy)2Cl2 and 180 mg (0.93 mmol) AgBF4. The reaction mixture was heated at reflux for 18 hrs, cooled, and then filtered through celite to afford a dark red/purple filtrate. The solvent was removed in vacuo and then passed through a silica column (MeCN:KN03(aq) 7: 1 v/v), followed by anion exchange with a saturated aqueous NH4PF methanolic solution to produce 52 mg of a red precipitate (yield = 19%). NMR (CD3CN): 6.61 (d, 1H, J = 8 Hz), 6.98 (dt, 1H, J = 7 Hz, 6 Hz, l = 1 Hz), 7.17-7.25 (m, 3H), 7.39, (dd, 1H, J = 8 Hz, l = 2 Hz), 7.42 (dt, 1H, J = 8 Hz, l = 1 Hz), 7.60 (d, 1H, J = 5 Hz), 7.69-7.75 (m, 3H), 7.78-7.87 (m, 4H), 7.95 (d, 1H, 3 J = 6 Hz), 7.99 (dt, 1H, J = 8 Hz, J = 2 Hz), 8.14 (d, 1H, J = 8 Hz), 8.31 (d, 1H, J = 7 Hz), 8.33 (d, 1H, J = 7 Hz), 8.38 (d, 1H, J = 8 Hz), 8.41 (d, 1H, l = 2 Hz), 8.46 (d, 1H, J = 8 Hz), 9.08 (vbr, 1H). ESI-MS: m/z, 612.1 (calcd for {M+} 612.1) Anal. Calcd. for C32H24F6N5O2PRU + 0.5 H20: C, 50.20; H, 3.29; N, 9.15. Found: C, 50.29; H, 3.49; N, 9.07.

Reference： [1]Patent: WO2011/32269,2011,A1 .Location in patent: Page/Page column 36

6
[ 4467-07-6 ]
[ 141-43-5 ]
[ 1440513-09-6 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81

7
[ 591-17-3 ]
[ 4467-07-6 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81

8
[ 109-04-6 ]
[ 4467-07-6 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81
[2]Patent: WO2014/100734,2014,A1
[3]Organic Letters,2015,vol. 17,p. 1513 - 1516
[4]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166

9
[ 4373-61-9 ]
[ 4467-07-6 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81
[2]Organic Letters,2015,vol. 17,p. 1513 - 1516

10
[ 4467-07-6 ]
[ 1440513-10-9 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81

11
[ 4467-07-6 ]
[ 1440513-11-0 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81

12
[ 4467-07-6 ]
[ 1440513-12-1 ]

Reference： [1]Inorganic Chemistry Communications,2013,vol. 32,p. 78 - 81

13
[ 98061-20-2 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With water; sodium hydroxide; In methanol; at 20℃; for 3.0h;	[00336] To a solution of methyl 3-(pyridin-2-yl)benzoate (400 mg, 1.88 mmol) in MeOH (3 mL) was added aqueous of NaOH (1 mL, 40 mol%). The reaction mixture was stirred at room temperature for 3 h and concentrated. The crude residue was dissolved in water and the pH was adjusted to 5-6 with 2N of HCl. The solution was extracted with ethyl acetate, brine, dried over sodium sulfate, filtered and concentrated. (350 mg, yield 93%) MS (ESI+) e/z: 200.1 [M+l]+.

Reference： [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00336
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166

14
[ 99769-19-4 ]
[ 4467-07-6 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166

15
[ 933713-75-8 ]
[ 4467-07-6 ]
[ 1616059-37-0 ]

Yield	Reaction Conditions	Operation in experiment
27%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 25℃; for 16.0h;	[00337] To a solution of <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> (60 mg, 0.30 mmol) in DCM (8 mL) was added EDCI (86 mg, 0.45 mmol), HOBt (61 mg, 0.45 mmol), Et3N (61 mg, 0.6 mmol) and l-amino-3-(isoindolin-2-yl)propan-2-ol (86 mg, 0.45 mmol). The mixture was stirred at 25 C for 16 h, washed with water and extracted with DCM. The combined organic extracts were concentrated, and the residue was purified by preparative HPLC purification. (30 mg, 27%) MS (ESI+) e/z: 374.2 [M+l]+ 1H NMR (MeOD, 400 MHz), delta ppm: 8.65 (d, J=4.8 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H), .96-1.92 (m, 3H), 7.62 (dd, J=7.2 Hz, 1H), 7.40-7.35 (m, 6H), 4.70 (s, 4H), 4.29 (br.s, 1H), 3.63-3.30 (m, 4H).

Reference： [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00337

16
[ 17933-03-8 ]
[ 4467-07-6 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1513 - 1516

17
[ 4467-07-6 ]
C₁₂H₁₀N₂O [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1513 - 1516

18
[ 4467-07-6 ]
C₂₀H₁₂N₂O₄ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1513 - 1516

19
[ 4467-07-6 ]
C₁₂H₈ClNO*ClH [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1513 - 1516

20
[ 4467-07-6 ]
tert-butyl (4-carbamoyl-2-(pyridin-2-yl)phenyl)carbamate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1513 - 1516

21
[ 4467-07-6 ]
1,3-dioxoisoindolin-2-yl 4-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)benzoate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1513 - 1516

22
[ 64-18-6 ]
[ 954279-15-3 ]
[ 4467-07-6 ]
N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-3-(pyridin-2-yl)benzamide formate salt [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166

23
[ 1616077-51-0 ]
[ 4467-07-6 ]
[ 1616246-07-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166

24
[ 1616077-53-2 ]
[ 4467-07-6 ]
[ 1616246-06-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166

25
2-fluorobenzenesulfonyl hydrazide [ No CAS ]
[ 4467-07-6 ]
C₁₈H₁₄FN₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 40℃; for 17.0h;Inert atmosphere;	The benzoc acid (1 eq.), sufony hydrazde (1.25 eq.), HOAt (1.25 eq.) and EDCLHC (1.25 eq.) were dssoved n MeCN (0.8 M), under an atmosphere of nitrogen. The souton washeated to 40C and aflowed to sUr for 17 hours, upon which time the reaction was cooed, concentrated in vacuo, then oaded drecUy onto sWca for purt1caDon. The crude matera was purfied by sWca g& chromatography (soera Botage, 0-100% EtOAc n petroeum benzne 40-60C). Product-contanng fractions were combned and concentrated in vacuo to give the tWe compound. The foHowng from the namedcompounds were synthessed accorcHng to the specfled Amde couphng (M) ntermedates (nt):41AP1Cccuress scUd (60% y&d). 1H NMR (400MHz, DMSO)6 10.88 (d, J=2.O Hz, 1H),10.35 (d, J= 2.3 Hz, 1H), 8.70 (d, J= 4.7Hz, 1 H), 8.42 (s, 1 H), 8.25 (d, J = 7.9 Hz,1H), 8.01 (d, J= 8.0 Hz, 1H), 7.93 (td, J7.7, 1.8 Hz, 1H), 7.82 (t, J= 7.5 Hz, 1H),7.75 (d, J = 7.8 Hz, 1 H), 7.69 (dd, J =13.6, 7.0 Hz, 1H), 7.57 (t, J= 7.8 Hz, 1H),7.41 (dd, J= 11.5, 6.7 Hz, 2H), 7.30 (t, J=8.0 Hz, 1 H).LCMS B rt 3.44 mn, m/z372.1 [M + H].

Reference： [1]Patent: WO2016/198507,2016,A1 .Location in patent: Page/Page column 41; 67; 68

26
[ 585-76-2 ]
[ 4467-07-6 ]

Reference： [1]Patent: WO2016/198507,2016,A1

27
[ 109-04-6 ]
[ 269409-73-6 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; N,N-dimethyl-formamide; at 110℃;Inert atmosphere;	To a degassed souton of DMF:H20 (10:1 raUo) (0.3 M), under an atmosphere of nitrogen, was added the pnaco ester (1 mmo), 2-bromopyrdne or 2-choropyrmdne (1 .5 eq.), and Cs2CO3 (4.4 eq.). The whoe mxture was degassed once agan and then Pd(PPh3)4 (5mo%) was added. The resutng souton was heated to 110C overnght. The sovent was removed in vacuo to give a dark gummy residue, which was taken up nto EtOAc and H20, then acdfied with 2 M HC to pH 2. The organic ayer was separated and the aqueous ayer was further extracted with EtOAc (2x). The combined organic ayers were dried over MgSO4 and concentrated in vacuo to gve a back ofly residue. The residue was dry oaded ontosWca ge in vacuo then purfied by flash coumn chromatography, eutng with 10-30% EtOAc/petroeum benzne and 1% acetic acid to afford the tWe compound.The foHowng compounds were made by Suzuk CoupUng F:P1B1Off white soUd (75% yed). 1H NMR (400 MHz,DMSO) 6 8.71 8.68 (m, 1 H), 8.67 (s, 1 H), 8.29 (d,J = 7.8 Hz, 1 H), 8.01 (t, J = 8.4 Hz, 2H), 7.91 (td, J =7.8, 1.8 Hz, 1 H), 7.61 (t, J = 7.7 Hz, 1 H), 7.42 7.37(m, 1H). LCMS B rt3.17, m/z200.1 [M + H].

Reference： [1]Patent: WO2016/198507,2016,A1 .Location in patent: Page/Page column 40; 50

28
N-(4-chlorophenyl)-5,5-difluoropiperidine-3-carboxamide [ No CAS ]
[ 4467-07-6 ]
N-(4-chlorophenyl)-5,5-difluoro-1-(3-(pyridin-2-yl)benzoyl)piperidine-3-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1744 - 1749

29
[ 4467-07-6 ]
N-(4-methyl-3-(3-(pyridin-2-yl)benzamido)phenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%		To a stirred solution of XXXVIII (0.09 g, 0.44 mmol) in 3 mL of DMF was added HATU (0.21 g,0.55 mmol) and stirred at RT for 5 minutes. XXXV (0.15 g, 0.37 mmol) and DIPEA (0.09 g, 0.73 mmol)were then added and reaction mixture was allowed to stir at RT for overnight. The crude mixture was dilutedwith ice cold water and extracted with ethyl acetate (20 mL x 3). Organic layer was washed with brinesolution, dried over anhydrous sodium sulphate and evaporated under vacuum to get the crude mass whichwas purified by reverse phase chromatography to obtain 17 (0.034, 13%).LCMS: 588 [M+1]+1HNMR (DMSO-d6, 400 MHz): delta 10.23 (s, 1H), 10.15 (s, 1H), 8.68 (d, 2H), 8.37 (d, 1H), 8.23 (m, 2H),8.15 (m, 2H), 7.94 (m, 2H), 7.82 (s, 1H), 7.64 (m, 2H), 7.42 (t, 1H), 7.24 (d, 1H), 3.65 (s, 2H), 2.43-2.26(m, 8H), 2.22 (s, 3H), 2.18 (s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2153 - 2160

30
(1-(3-aminophenyl)piperidin-4-yl)(4-methylpiperazin-1-yl)methanone [ No CAS ]
[ 4467-07-6 ]
N-(3-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)phenyl)-3-(pyridin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; ethyl acetate; at 20℃; for 20.0h;	General procedure: 4 (0.1 g, 0.0002 mol), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidhexafluorophosphate (HATU, 0.2 g, 0.0004 mol), and substituted benzoic acid (0.0003 mol) weredissolved in 2 mL of dichloromethane followed by DIPEA (1 g, 0.7 mmol), the reaction was allowed toreact at room temperature for 20 h, 20 mL of methylene chloride was added, and the reaction solutionwas washed with saturated sodium bicarbonate solution (10 mL x 2). The reaction solution was driedover anhydrous sodium sulfate and evaporated to dryness under reduced pressure to give a yellowoil which was purified by column chromatography on silica gel (n-hexane:ethyl acetate = 10:1) to getproduct 5a-q.

Reference： [1]Molecules,2018,vol. 23

31
[ 1432795-28-2 ]
[ 585-76-2 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere;	General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 mol%) and further degassed (5times). The resulting mixture was stirred at 95 C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100%) to yield the desired product.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 634 - 648

32
[ 4467-07-6 ]
[ 80-17-1 ]
N'-(3-(pyridin-2-yl)benzoyl)benzenesulfonohydrazide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 4655 - 4684

33
7-amino-N-methyl-3,4-dihydroquinoline-1(2H)-carboxamide [ No CAS ]
[ 4467-07-6 ]
N-methyl-7-(3-(pyridin-2-yl)benzamido)-3,4-dihydroquinoline-1(2H)-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		To a solution of <strong>[4467-07-6]3-(pyridin-2-yl)benzoic acid</strong> (DC_4, 40 mg, 0.2 mmol) in DCM (5mL) was added HATU (114 mg, 0.3 mmol), DIPEA (78 mg, 0.6 mmol),and the mixture was stirred for 0.5 h before 7-amino-N-methyl-3,4-dihydroquinoline-1(2H)-carboxamide (DC_3, 42 mg, 0.2 mmol) was added. The mixture was stirred continuously for 3 h at rt and concentrated in vacuo. The residue was purified by silica gel chromatography (DCM/MeOH = 50:1) to afford the title compound (DC-CPin709, 34 mg, 44%) as a pale yellow oil.

Reference： [1]Bioorganic Chemistry,2020,vol. 101

34
[ 4467-07-6 ]
[ 23380-75-8 ]

Reference： [1]Science,2021,vol. 372,p. 1452 - 1457

35
[ 4467-07-6 ]
(S)-2-(3-(4-phenyl-1-(p-tolyl)-4,5-dihydro-1H-imidazole-2-yl)phenyl)pyridine [ No CAS ]