[ CAS No. 904326-87-0 ]

Name: 904326-87-0|N-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide|95+%
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SKU: A292759
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Quality Control of [ 904326-87-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 904326-87-0 ]

SDS Specification

Alternatived Products of [ 904326-87-0 ]

Product Details of [ 904326-87-0 ]

CAS No. :	904326-87-0	MDL No. :	MFCD08690229
Formula :	C₁₃H₁₉BN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YCWPTBAHVWJMEY-UHFFFAOYSA-N
M.W :	262.11 g/mol	Pubchem ID :	17750202
Synonyms :

Calculated chemistry of [ 904326-87-0 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	75.03
TPSA :	60.45 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) :	-6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.35
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.04
Log Po/w (SILICOS-IT) :	0.91
Consensus Log Po/w :	0.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	1.17 mg/ml ; 0.00445 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	1.57 mg/ml ; 0.006 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.01
Solubility :	0.0254 mg/ml ; 0.0000968 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.93

Safety of [ 904326-87-0 ]

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 [ 904326-87-0 ]

* 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.

Downstream synthetic route of [ 904326-87-0 ]

[ 904326-87-0 ] Synthesis Path-Downstream 1~41

1
[ 7169-97-3 ]
[ 73183-34-3 ]
[ 904326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
89.1%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃;Inert atmosphere; Industrial scale;	A 1 L four-necked flask equipped with a magnetic stirrer, a thermometer, a reflux condenser and a bubbler was charged56.41 g (0.264 mol) of 2-acetylamino-5-bromopyridine, 66.02 g (0.26 mol) of bis (pinacolato) diboron and 76.44 g450 mL of dioxane was added and stirred, 1.90 g (0.002589 mol) of ferrocenepalladium chloride was added under the protection of nitrogen, and the mixture was heated to 100 C. for 18 to 24 hours,TLC control to the end of the reaction, the temperature was precipitated solids, beating filtration, methanol was added 500mL dissolved, filtered and evaporated to dryness, plus heptane beating, to give the product 60.08g, yield 89.1%.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃; for 15h;	Method 32; iV-\|'5-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl')pyridin-2-yl1acetamide; A mixture of JV"-(5-bromopyridin-2-yl)acetamide (Method 31; 0.450 g, 2.09 mmol), bis(pinacolato)diboron (0.585 g, 2.30 mmol), potassium acetate (0.616 g, 6.27 mmol), and Pd(dppf)Cl2 (0.077 g, 0.105 mmol) in DMF (10 ml) was stirred at 80 0C for 15 h. The reaction mixture was filtered over diatomaceous earth, concentrated under reduced pressure and the residue was used without further purification, m/z 263.
		A solution of 2-acetylamino-5-bromopyridine (0.25 g, 0.95 mmol), bispinacolatodiboron (0.27 g, 1.04 mmol) and KOAc (0.14 g, 1.42 mmol) in 1 ,4- dioxane (8.0 mL) was degassed by flushing with nitrogen for 15 min. Tricyclohexylphosphine (0.032 g, 0.11 mmol) and tris(dibenzyledineacetone) dipalladium (0) (0.05 g, 0.047 mmol) was then added to the reaction mixture, which was again degassed by nitrogen for 15 min. The resulting reaction mixture was heated to 8O0C for 3 h. After the completion of the reaction (TLC monitoring), the reaction mixture was filtered through celite bed and the filtrate was concentrated to get the crude residue that was carried forward to the next step without further purification. MS: 263.15 (M+H)+.

Reference： [1]Patent: CN103601745,2017,B .Location in patent: Paragraph 0031; 0032
[2]Patent: WO2006/79791,2006,A1 .Location in patent: Page/Page column 42
[3]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 36

2
[ 827614-64-2 ]
[ 108-24-7 ]
[ 904326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
63.1%	With dmap; triethylamine; In dichloromethane; at 20℃;	1. Preparation of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300mg, 1.36mmol) in dichlormethane(15mL) were successively added dimethylaminopyridine(17mg, 0.139mmol), triethylamine(0.21mL, 1.50mmol) and acetic anhydride(153mg, 1.50mmol). The resulting mixture was reacted under stirring at room temperature for several hours. Then the reaction mixture was diluted with dichlormethane, and washed with aqueous saturated ammonium chloride solution. The organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated to produce 225 mg of the target compound in a yield of 63.1%.
52%	With dmap; triethylamine; In dichloromethane; at 20℃; for 3.5h;	EXAMPLE 9; Procedures for the Synthesis ofN-(5-(7-Chloro-3-(2-chlorobenzyl)-2-oxo-2,3-dihydro-lH- benzo[e][l,4]diazepin-5-yl)pyridin-2-yl)acetamide; Beginning with Tetramethyl-1,3,2- dioxaborolan-2-yl)pyridin-2-amine.; Step l; N-(5-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide. 5 (4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.3 g, 1.36 mmol) was dissolved in dichloromethane (5 niL) and 4-dimethylaminopyridine 17 mg, 0.136 mmol) was added, followed by triethylamine (0.38 mL, 2.73 mmol) then acetic anhydride (0.153, 1.5 mmol). The mixture was stirred at room temperature for 3.5 h then diluted with dichloromethane and washed with NH4Cl (sat aq) then brine. The organic layer was dried (MgSO4), filtered and concentrated. Chromatography eluting with ethyl acetate gave the desired product (187 mg, 52% yield). 1H-NMR (300 MHz, CDCl3) delta 9.3 (s, IH), 8.6 (s, IH), 8.2 (d, IH), 8.05 (d, IH), 2.2 (s, 3H), 1.2 (s, 12H).
	With triethylamine; In dichloromethane; at 20℃;	To 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (120 mg) in dry DCM (3ml) and triethylamine (1.5equiv., 114uL) was added acetic anhydride(l.lequiv., 57ul) and the reaction mixture was stirred at room temperature overnight.Dichloromethane/brine extraction and purification on silica gave 66mg of N-[5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-yl]-acetamide.[00584] 2-Chloro-6-(4-methanesulfonyl-piperazin- 1 -ylmethyl)-4-morpholin-4-yl- thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, was reacted with N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-yl]-acetamide via General ProcedureA. Purification on silica and ether trituration gave 233. NMR (CDC13): 2.25 (3H, s), 2.67-2.71 (4H, m), 2.81 (3H, s), 3.29-3.33 (4H, m), 3.89 (2H, s), 3.89-3.93 (4H, m), 4.08-4.12 (4H, m), 7.35 (IH, s), 7.97 (IH, br. s), 8.28 (IH, d), 8.71 (IH, d), 9.30 (IH, s). MS (ESI+): MH+532.28 (100%)

225mg	With dmap; triethylamine; In dichloromethane; at 20℃; for 0.5h;	4-dimethylaminopyridine (17mg, 0.139mmol), triethylamine (0.19 mL, 1.36mmol) and acetic anhydride (153mg, 1.50mmol) were added sequentially to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300mg, 1.36mmol) in dichloromethane (15mL). The reaction mixture was stirred at room temperature for 0.5 h, then diluted with 30mL of dichloromethane, washed with 50mL of a saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 225mg of the product.
225 mg	With dmap; triethylamine; In dichloromethane; at 20℃; for 0.5h;	4-dimethylaminopyridine (17 mg, 0.139 mmol), triethylamine (0.19 mL, 1.36 mmol) and acetic anhydride (153 mg, 1.50 mmol) were added sequentially to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300 mg, 1.36 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 0.5 h, then diluted with 30 mL of dichloromethane, washed with 50 mL of a saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 225 mg of the product.

Reference： [1]Patent: EP2719697,2014,A1 .Location in patent: Paragraph 0152-0154
[2]Patent: WO2010/121164,2010,A2 .Location in patent: Page/Page column 79
[3]Patent: WO2008/70740,2008,A1 .Location in patent: Page/Page column 179
[4]Patent: EP2781520,2014,A1 .Location in patent: Paragraph 0123 - 0125
[5]Patent: US2015/166539,2015,A1 .Location in patent: Paragraph 0263; 0264; 0265

3
[ 904326-87-0 ]
[ 1160789-85-4 ]
[ 1160790-20-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide; 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h; Stage #2: In water; N,N-dimethyl-formamide at 85℃; for 2.25h;	26 A solution of N-(5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide H-B (0.13 g, 0.49 mmol), 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea (0.10 g, 0.33 mmol) and K3PO4 (0.084 g, 0.39 mmol) in DMF-H2O (7.0 mL, 5:2) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)-palladium(ll) (0.023 g, 0.033 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 850C for 2 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 (60-120 M, 2.50% MeOH-DCM) to obtain the desired product (0.057 g, 48%). 1H-NMR (400 MHz, DMSO-d6): δ 1.09 (t, J= 7.20 Hz, 3H), 2.11 (S, 3H), 3.21 (m, 2H), 6.73 (br s, 1 H), 7.55 (d, J= 9.20 Hz, 1 H), 7.92-7.97 (m, 2H)1 8.15 (m, 2H), 8.68 (s, 1 H), 10.58 (br s, 1H) and 10.74 (br s, 1H). MS: 354.09 (M+H) Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 264 nm): 93.67% (Rt = 4.83 min).

Reference： [1]Current Patent Assignee: SPERO THERAPEUTICS INC - WO2009/74812, 2009, A1 Location in patent: Page/Page column 37-38

4
[ 904326-87-0 ]
[ 1160789-85-4 ]
[ 1160790-42-0 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide; 1-(5-bromobenzo[d]thiazol-2-yl)-3-ethylurea With potassium phosphate In water; N,N-dimethyl-formamide for 0.25h; Stage #2: In water; N,N-dimethyl-formamide at 110℃; for 2.25h;	38 A solution of 1-(5-bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea V (0.10 g, 0.31 mmol), N-(5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (0.17 g, 0.62 mmol) and K3PO4 (0.067 g, 0.31 mmol) in DMF-H2O (2.5 ml_, 2:0.5) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)- palladium(ll) (0.022 g, 0.031 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 11O0C for 2 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 (3 x 25 mL). The combined organics was washed with brine, dried (Na2SO^, filtered and concentrated under reduced pressure. The crude was then purified over silica gel (100-200 M, 1.5% MeOH-DCM) and then through prep-HPLC to obtain the desired product (0.046 g, 39%). 1H-NMR (400 MHz, DMSO-d6): δ 1.08 (t, J= 7.20 Hz, 3H), 2.12 (s, 3H), 3.20 (quintet, J= 6.40 Hz, 2H), 6.77 (br s, 1 H), 7.75 (d, J= 6.80 Hz, 1 H)1 7.93 (d, J= 10.40 Hz, 1 H)1 8.01 (d, J= 8.40 Hz, 1H), 8.18 (d, J= 8.80 Hz, 1 H), 8.52 (s, 1H)1 10.63 (br s, 1H) and 10.85 (br s, 1H). MS: 374.20 (M+H)+. Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 261 nm): 98.72% (Rt = 5.03 min).

Reference： [1]Current Patent Assignee: SPERO THERAPEUTICS INC - WO2009/74812, 2009, A1 Location in patent: Page/Page column 49

5
[ 904326-87-0 ]
[ 1233524-18-9 ]
[ 1233524-20-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1,4-dioxane; water at 120℃; for 2h;	3 Example 3 N-(5-{2-[2-Amino-6-(4-methylpiperazin-l-yl)pyriiiιidin-4-yl]-l^^,4-tetrahydroisoquinolin-7- yl}pyridin-2-yl)acetamide; A mixture of 4-(7-bromo-3,4-dihydroisoquinolin-2( 1 H)-y I)-6-(4-methy Ipiperazin- 1 -yl)pyrimidin- 2-amine (15 mg, 0.037 mmol, Example 1), N-[5-(4,4,5,5-tetrarnethyl-l,3,2-dioxaborolan-2-yl)pyridiϖ-2- yl]acetamide (15 mg, 0.056 mmol, Aldrich, Cat. No. 683892), tetrakis(triphenylphosphine)palladium(0) (2.6 mg, 0.0022 mmol, Aldrich, Cat. No. 216666), and potassium phosphate (24 mg, 0.1 1 mmol) in 1,4- dioxane (1 mL) and water (0.2 mL) was heated at 120 0C for 2 hours. The reaction mixture was cooled to r.t. and then concentrated. The residue was dissolved in MeOH and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS (M+H)+: m/z = 459.4.

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2010/75270, 2010, A1 Location in patent: Page/Page column 60-61

6
[ 904326-87-0 ]
[ 1059065-41-6 ]
[ 1251949-00-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With cesium hydroxide; lithium chloride In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;	9.2 Step 2; N-(5-(7-Chloro-3-(2-chlorobenzyl)-l-(4-methoxybenzyl)-2-oxo-2,3-dihydro-lH- benzo[e][l,4]diazepin-5-yl)pyridin-2-yl)acetamide. 5,7-Dichloro-3-(2-chlorobenzyl)-l-(4- methoxybenzyl)-lH-benzo[e][l,4]diazepin-2(3H)-one (208 mg, 0.439 mmol), LiCl (56 mg, 1.32 mmol), and CsOH (221 mg, 1.32 mmol) were combined, then a solution of N-(5- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (115 mg, 0.439 mmol) in 1,4-dioxane (3 mL) was added followed by water (300 uL). The mixture was purged with nitrogen, then tetrakis(triphenylphosphinepalladium(0) (51 mg, 0.044 mmol) was added and the flask was lowered into a 100 0C oil bath and heated at 100 0C for 3 h. The mixture was allowed to cool, then diluted with ethyl acetate and rinsed with water 2x then brine and dried (MgSO4). Chromatography eluting with 40-50% ethyl acetate in hexanes to give a colorless oil (210 mg, 83% yield). MS (ES+) m/z 573.1 (M + 1).

Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2010/121164, 2010, A2 Location in patent: Page/Page column 79-80

Yield	Reaction Conditions	Operation in experiment
57%
57%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere;	63.63b Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107) General procedure: Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107)[0334]To a solution of compound 0601-107 (2.5 g, 11.6 mmol) and bis(pinacolato)diboron (4.4 g, 17.5 mmol) in dioxane (100 mL) was added potassium acetate (3.4 g, 35 mmol) and PdCl2(dppf)2 (0.95 g, 1.1 mmol). The mixture was degassed with nitrogen and heated at 85° C. for overnight. The reaction mixture was concentrated under reduced pressure to afford the crude product, which purified by column chromatography (ethyl acetate in petroleum ether, 15% v/v) to give the compound 0602-107 (1.55 g, 51%) as a pink solid. LCMS: 262 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (s, 12H), 2.03 (s, 3H), 7.30 (s, 1H), 7.31 (d, J=2.0 Hz 1H), 7.73 (d, J=2.0 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 9.93 (s, 1H).
57%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere;	63b N-(3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) acetamide (Compound 0602-107) General procedure: Compound in dioxane (100mL) 0601-107 (2.5g, 11.6mmol) and a solution of bis (pinacolato) diboron (4.4 g, 17.5 mmol), potassium acetate (3.4 g, 35 mmol) and and PdCl2 (dppf) 2 ( 0.95g, 1.1mmol) was added. The mixture was degassed with nitrogen and heated overnight at 85 ° C.. The reaction mixture was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether in ethyl acetate, 15% v / v) to give the compound 0602-107 as a pink solid obtained (1.55 g, 51%).

8
[ 904326-87-0 ]
[ 1346702-51-9 ]
[ 1346704-16-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 120℃; for 0.333333h; Inert atmosphere; Sealed tube; Microwave irradiation;	108 Example 1086-[6-(Acetylamino)-3-pyridinyl]-W-[(4,6-dimethyl-2-oxo- l,2-dihydro-3-pyridinyl)methyl]- 1 -(1 - m deIn a 25 mL sealable tube under nitrogen were combined 6-bromo-N-[(4,6-dimethyl-2-oxo- l,2-dihydro-3-pyridinyl)methyl]-l-(l-methylethyl)-lH-indazole-4-carboxamide (110 mg, 0.24 mmol), N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridinyl]acetamide (104 mg, 0.4 mmol) in DME/water (3 mL: lmL). PdCl2(dppf)-CH2Cl2 (10.76 mg, 0.013 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (66.4 mg, 0.79 mmol) was added, the vessel was sealed, and the insoluble mixture was heated in a microwave at 120 °C for 20 min. Water was added and the solids that precipitated were filtered off. DCM was added to the solids and it was purified by Si02 chromatography (eluent: gradient 100% DCM to 80:20:2DCM/MeOH/NH4OH). Fractions were evaporated. EtOAc was added, it was sonicated and the solids that precipitated were filtered, washed with hexanes and dried to afford the title compound (91 mg, 72%) as a light beige solid. *H NMR (400 MHz, DMSO-c¾) δ ppm 1 1.54 (s, 1 H) 10.65 (s, 1 H) 8.84 (d, J=2.27 Hz, 1 H) 8.64 (t, J=4.93 Hz, 1 H) 8.39 (s, 1 H) 8.25 - 8.30 (m, 1 H) 8.15 - 8.24 (m, 2 H) 7.89 - 7.93 (m, 1 H) 5.89 (s, 1 H) 5.18 (quin, J=6.63 Hz, 1 H) 4.40 (d, J=4.80 Hz, 2 H) 2.22 (s, 3 H) 2.13 (s, 3 H) 2.12 (s, 3 H) 1.51 (s, 3 H) 1.50 (s, 3 H). MS(ES) [M+H]+ 473.1.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/140325, 2011, A1 Location in patent: Page/Page column 129

9
[ 904326-87-0 ]
[ 1332450-86-8 ]
[ 1332448-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere;	71 Example No. 71; Preparation of Compound No. 71[0368] To a de-aerated solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.28 mmol), N-methyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)picolinamide (148 mg, 0.56 mmol) and K2C03 (115 mg, 0.84 mmol) in DME-water (2: 1) was added Pd(PPh3)4 (16 mg, 0.014 mmol). The reaction mixture was stirred at 90 °C for 2h, additional Pd (PPh3)4 (16 mg, 0.014 mmol) was added into the reaction mixture and stirring continued at 90 °C for 12h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc(30 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 5-(2-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)- yl)phenyl)-N-methylpicolinamide as an off-white solid. 1H NMR (TFA salt, CD3OD) d (ppm): 8.21 (d, IH), 7.82 (d, IH), 7.76 (m, 3H), 7.6 (d, 2H), 7.23 (s, IH), 6.9 (d, 2H), 4.7 (m, IH), 4.3 (m, IH), 3.63 (m, IH), 3.42 (m, IH), 2.8-3.1 (m, 7H), 2.6 (m, IH), 2.4 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 187

10
[ 904326-87-0 ]
[ 1332450-86-8 ]
[ 1332448-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h; Inert atmosphere;	83 Example No. 83; Preparation of Compound No. 83[0380] To a de-aerated solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.562 mmol) and K2C03 (116 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The reaction mixture was concentrated under reduced pressure to dryness. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield N-(5-(2-(2,8-dimethyl-3,4- dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)pyridin-2-yl)acetamide as a TFA salt. 1H NMR (TFA salt, CD3OD) d (ppm): 7.8-8.0 (m, 2H), 7.6-7.78 (m, 3H), 7.35-7.48 (m, 2H), 7.27 (s, 1H), 7.0 (d, 1H), 6.9 (d, 1H), 4.63 (d, 1H), 4.3 (d, 1H), 3.64 (m, 1H), 3.42 (m, 1H), 2.92-3.1 (m, 4H), 2.8 (m, 1H), 2.4 (s, 3H), 2.1 (s, 3H).
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h;	83 Example No. 83: Preparation of Compound No. 83[0371] To a de-aerated solution of 5-(2-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.562 mmol) and K2C03 (116 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The reaction mixture was concentrated under reduced pressure to dryness. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield N-(5-(2-(2,8-dimethyl-3,4-dihydro-lH- pyrido[4,3-b]indol-5(2H)-yl)phenyl)pyridin-2-yl)acetamide as a TFA salt. 1H NMR (TFA salt, CD3OD) δ (ppm): 7.8-8.0 (m, 2H), 7.6-7.78 (m, 3H), 7.35-7.48 (m, 2H), 7.27 (s, IH), 7.0 (d, IH), 6.9 (d, IH), 4.63 (d, IH), 4.3 (d, IH), 3.64 (m, IH), 3.42 (m, IH), 2.92-3.1 (m, 4H), 2.8 (m, IH), 2.4 (s, 3H), 2.1 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 192
[2]Current Patent Assignee: PFIZER INC - WO2012/112962, 2012, A1 Location in patent: Page/Page column 166

11
[ 904326-87-0 ]
[ 1332450-87-9 ]
[ 1332448-42-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere; Reflux;	56 Example No. 56; Preparation of Compound No. 56[0353] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.25 mmol) in DME (2 mL) were added water (1 mL) and K2C03 (110 mg, 0.77 mmol) and purged the solution with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and 2-acetamidopyridine-5-boronic acid pinacol ester (140 mg, 0.515 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled to RT and diluted with EtOAc. Aqueous layer was extracted with EtOAc (3x6 mL) and the combined organic layer dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) d (ppm): 8.0 (s, IH), 7.8 (m, 2H), 7.68 (m, IH), 7.51 (m, IH), 7.33 (s, IH), 6.82-7.0 (m, 2H), 4.77 (d, IH), 4.4 (d, IH), 3.78 (m, IH), 3.5 (m, IH), 3.1 (m, 4H), 2.7 (m, IH), 2.4 (s, 3H), 2.2 (s, 3H).
	With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere;	56 Example No. 56: Preparation of Compound No. 56[0344] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro- 1H- pyrido[4,3-b]indole (100 mg, 0.25 mmol) in DME (2 mL) were added water (1 mL) and K2C03 (110 mg, 0.77 mmol) and purged the solution with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and 2- acetamidopyridine-5-boronic acid pinacol ester (140 mg, 0.515 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled toRT and diluted with EtOAc. Aqueous layer was extracted with EtOAc (3x6 mL) and the combined organic layer dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR(TFA salt, CD3OD) δ (ppm): 8.0 (s, IH), 7.8 (m, 2H), 7.68 (m, IH), 7.51 (m, IH), 7.33 (s, IH),6.82-7.0 (m, 2H), 4.77 (d, IH), 4.4 (d, IH), 3.78 (m, IH), 3.5 (m, IH), 3.1 (m, 4H), 2.7 (m, IH),2.4 (s, 3H), 2.2 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 181
[2]Current Patent Assignee: PFIZER INC - WO2012/112962, 2012, A1 Location in patent: Page/Page column 157

12
[ 904326-87-0 ]
[ 1332450-87-9 ]
[ 1332448-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Inert atmosphere; Reflux;	73 Example No. 73; Preparation of Compound No. 73[0370] To a solution of 5-(4-bromothiophen-3-yl)-2,8-dimethyl-2,3,4,5-tetrahydro- 1H- pyrido[4,3-b]indole (100 mg, 0.276 mmol) in DME-water (2: 1) was added K2C03 (110 mg, 0.77 mmol) and the solution purged with N2. Pd(PPh3)4 (20 mg, 0.017 mmol) and N-methyl- 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (145 mg, 0.552 mmol) were added to the reaction mixture, which was refluxed under N2 for 45 min. The reaction mixture was cooled to RT and extracted with EtOAc. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) d (ppm): 8.1-8.27 (m, IH), 8.0 (s, IH), 7.8 (m, 2H), 7.42 (m, IH), 7.3 (s, IH), 6.9-7.0 (m, 2H), 4.76 (d, IH), 4.38 (d, IH), 3.7 (m, IH), 3.5 (m, IH), 3.0 (m, 4H), 2.88 (s, 3H), 2.93 (m, IH), 2.4 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 188

13
[ 904326-87-0 ]
[ 1332450-89-1 ]
[ 1332448-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 0.75h; Inert atmosphere;	45 Example No. 45; Preparation of Compound No. 45[0342] To a de-aerated solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.560 mmol) and K2C03 (120 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The solvent was removed under reduced pressure, residue diluted with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield N-(5-(3-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)- yl)phenyl)pyridin-2-yl)acetamide. 1H NMR (TFA salt, CD3OD) d (ppm): 8.6 (s, 1H), 8.18 (s, 2H), 7.8 (d, IH), 7.62-7.77 (m, 2H), 7.42 (d, IH), 7.3 (s, IH), 7.17 (d, IH), 7.03 (d, IH), 4.7 (d, IH), 4.42 (d,lH), 3.8 (m, IH), 3.58 (m, IH), 3.0-3.2 (m, 5H), 2.41 (s, 3H), 2.2 (s, 3H).
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h;	45 Example No. 45: Preparation of Compound No. 45[0333] To a de-aerated solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (100 mg, 0.281 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (147 mg, 0.560 mmol) and K2C03 (120 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh )4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 45 min. The solvent was removed under reduced pressure, residue diluted with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield N-(5-(3-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)pyridin-2- yl)acetamide. 1H NMR (TFA salt, CD3OD) δ (ppm): 8.6 (s, 1H), 8.18 (s, 2H), 7.8 (d, 1H), 7.62- 7.77 (m, 2H), 7.42 (d, 1H), 7.3 (s, 1H), 7.17 (d, 1H), 7.03 (d, 1H), 4.7 (d, 1H), 4.42 (d,lH), 3.8 (m, 1H), 3.58 (m, 1H), 3.0-3.2 (m, 5H), 2.41 (s, 3H), 2.2 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 176-177
[2]Current Patent Assignee: PFIZER INC - WO2012/112962, 2012, A1 Location in patent: Page/Page column 153

14
[ 904326-87-0 ]
[ 1332450-89-1 ]
[ 1332448-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.75h; Inert atmosphere;	75 Example No. 75; Preparation of Compound No. 75[0372] To a degassed solution of 5-(3-bromophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-lH- pyrido[4,3-b]indole (101 mg, 0.286 mmol), N-methyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)picolinamide (150 mg, 0.57 mmol) and K2C03 (236 mg, 1.71 mmol) in DME- water (2: 1) was added Pd(PPh3)4 (33 mg, 0.028 mmol). The reaction mixture was stirred at 90 °C for 45 min. The reaction mixture concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 5-(3-(2,8-dimethyl-3,4-dihydro- lH-pyrido[4,3-b]indol-5(2H)-yl)phenyl)-N-methylpicolinamide. 1H NMR (TFA salt, CD3OD) d (ppm): 8.97 (s, 1H), 8.23 (d, 1H), 8.12 (d, 1H), 7.85 (d, 1H), 7.78 (m, 2H), 7.5 (d, 1H), 7.37 (s, 1H), 7.21 (d, 1H), 7.04 (d, 1H), 4.76 (m, 1H), 4.4 (m, 1H), 3.8 (m, 1H), 3.6 (m, 1H), 3.08-3.21 (m, 5H), 3.0 (s, 3H), 2.4 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 188-189

15
[ 904326-87-0 ]
[ 1332450-92-6 ]
[ 1332449-35-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere;	105 Example No. 105Preparation of Compound No. 139[0402] To a de-aerated solution of 5-(5-bromopyridin-2-yl)-2,8-dimethyl-2,3,4,5- tetrahydro-lH-pyrido[4,3-b]indole (100 mg, 0.280 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (146 mg, 0.557 mmol) and K2C03 (116 mg, 0.839 mmol) in DME (4 mL) and water (2 mL) was added Pd(PPh3)4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for 2h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude material, which was purified by reverse HPLC to yield N-(6'-(2,8-dimethyl-3,4- dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)-3,3'-bipyridin-6-yl)acetamide as the TFA salt. 1H NMR (CD3OD, TFA salt) d (ppm): 8.9 (s, IH), 8.63 (s, IH), 8.3 (d, IH), 8.22 (d, IH), 8.18 (d, IH), 7.76 (d, IH), 7.5 (d, IH), 7.38 (s, IH), 7.13 (d, IH), 4.7 (d, IH), 4.4 (d, IH), 3.82 (bs, IH), 3.42-3.6 (m, 3H), 3.18 (s, 3H), 2.42 (s, 3H), 2.2 (s, 3H).
	With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h;	105 Example No. 105: Preparation of Compound No. 139 . . + \| 03 j ιο a ae-aerated solution or ^-(S-bromopyridin-z-ylj-z^-dimetnyi-z ^ -ieiranydro- lH-pyrido[4,3-b]indole (100 mg, 0.280 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (146 mg, 0.557 mmol) and K2C03 (116 mg, 0.839 mmol) in DME (4 mL) and water (2 mL) was added Pd(PPh )4 (16 mg, 0.013 mmol). The reaction mixture was stirred at 90 °C for2h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude material, which was purified by reverse HPLC to yield N-(6'-(2,8-dimethyl-3,4-dihydro-lH-pyrido[4,3-b]indol-5(2H)-yl)-3,3'-bipyridin-6-yl)acetamide as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm):8.9 (s, IH), 8.63 (s, IH), 8.3 (d, IH), 8.22 (d, IH), 8.18 (d, IH), 7.76 (d, IH), 7.5 (d, IH), 7.38(s, IH), 7.13 (d, IH), 4.7 (d, IH), 4.4 (d, IH), 3.82 (bs, IH), 3.42-3.6 (m, 3H), 3.18 (s, 3H), 2.42(s, 3H), 2.2 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2011/103430, 2011, A1 Location in patent: Page/Page column 201
[2]Current Patent Assignee: PFIZER INC - WO2012/112962, 2012, A1 Location in patent: Page/Page column 173-174

16
N-[(3S,3aS)-7-bromo-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide [ No CAS ]
[ 904326-87-0 ]
[ 1341208-75-0 ]

Yield	Reaction Conditions	Operation in experiment
35.3%	With potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,4-dioxane at 80℃; for 2h;

Reference： [1]Xin, Qisheng; Fan, Houxing; Guo, Bin; He, Huili; Gao, Suo; Wang, Hui; Huang, Yanqin; Yang, Yushe [Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7493 - 7502]

17
[ 904326-87-0 ]
[ 1354288-75-7 ]
[ 1354287-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tricyclohexylphosphine In 1,4-dioxane; water at 90℃; for 19h; Inert atmosphere;	167 5,7-Difluoro-N-(5-iodo-2-morpholinopyridin-4-yl)-3-methyl-2-(pyridin-2-yl)- quinolin-4-amine (94 mg, 0.17 mmol), 2-acetamidopyridine-5-boronic acid pinacol ester (89 mg, 0.34 mmol), tricyclohexylphosphine (10 mg, 0.037 mmol), and tris(dibenzylideneacetone)dipalladium (0) (16 mg, 0.018 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1 ,4-dioxane (2.5 mL) and aq. 1.3 M potassium phosphate tribasic (0.33 mL, 0.43 mmol) were added by syringe. The resulting reaction was heated to 90 °C and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-65 % of a premixed solution of 89:9: 1 DCM: MeOH: ammonium hydroxide in DCM) to afford a film that was further purified with HPLC (5-90% of 0.1% TFA acetonitrile solution in 0.1% TFA water solution.) The desired fractions were concentrated then diluted with EtOAc. After washing twice with saturated aq. sodium bicarbonate solution and once with brine, the solvent was removed under reduced pressure to yield a light yellow solid that was purified using SFC to afford a faint yellow solid as N- (4'-(5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-6'-morpholino- 3,3*-bipyridin-6-yl)acetamide. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.53 (1 H, s), 8.74 (1 H, m), 8.30 (1 H, d, J=2.4 Hz), 8.13 (3 H, m), 7.87 (1 H, d, J=7.8 Hz), 7.82 (1 H, s), 7.77 (1 H, dd, J=8.6, 2.2 Hz), 7.63 (1 H, dd, J=9.7, 2.1 Hz), 7.52 (1 H, ddd, J=7.6, 4.9, 1.0 Hz), 7.46 (1 H, ddd, J=12.5, 9.5, 2.4 Hz), 5.63 (1 H, s), 3.67 (4 H, m), 3.28 (4 H, m), 2.25 (3 H, s), 2.10 (3 H, s). Mass Spectrum (pos.) m/e: 568.2 (M+H)+.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2012/3283, 2012, A1 Location in patent: Page/Page column 251

18
[ 904326-87-0 ]
[ 10375-59-4 ]
[ 1374450-57-3 ]

Yield	Reaction Conditions	Operation in experiment
18 %Chromat.	With potassium fluoride; copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; [2.2.2]cryptande In N,N-dimethyl-formamide at 100℃; for 0.0833333h; Sealed vial;

Reference： [1]Riss, Patrick J.; Lu, Shuiyu; Telu, Sanjay; Aigbirhio, Franklin I.; Pike, Victor W. [Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2698 - 2702]

19
[ 904326-87-0 ]
[ 1432063-18-7 ]
7-acetamido-2-(3-(2-acetamidopyridinyl))quinoline-5,8-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	Stage #1: N-(2-chloro-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,3-dioxane for 0.166667h; Inert atmosphere; Stage #2: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide With potassium phosphate In 1,3-dioxane at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;

Reference： [1]Keyari, Charles M.; Kearns, Alison K.; Duncan, Nathan S.; Eickholt, Emily A.; Abbott, Geoffrey; Beall, Howard D.; Diaz, Philippe [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3806 - 3819]

20
[ 904326-87-0 ]
[ 1416000-57-1 ]
[ 1415999-92-6 ]

Yield	Reaction Conditions	Operation in experiment
42.2%	With sodium carbonate In dichloromethane	9.2 2. 2. Preparation of N-(5-(9-oxo-10-(3-(trifluoromethyl)phenyl)-9,10-dihydropyrido[3,2-c][1,5]naphthyridin-2-yl)pyridin-2-yl)acetamide To N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (225 m g, 0.858 mmol) were added 2-chloro-10-(3-(trifluoromethyl)phenyl)pyrido[3,2-c][1,5]naphthyridin-9(10H)-one (300 mg, 0.799 mmol), palladium tetrakis(triphenylphosphine)(15 mg) and 2N sodium carbonate solution (1.3 mL). This system was reacted in a nitrogen-protecting atmosphere at 90° C. for 16 hrs. The reaction mixture was cooled to room temperature and filtered. The organic layer was separated out, concentrated in a reduced pressure, dissolved in dichlormethane, successively washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and purified with a silica-gel column chromatography (ethyl acetate) to produce 160 mg of the target compound in a yield of 42.2%. Formula: C25H6F3N5O2 MW: 475.13 MS (M+H): 476.2 1H-NMR (d6-DMSO, 400 MHz): δ 10.65 (1H, s), 9.23 (1H, s), 8.46 (1H, d), 8.37 (1H, d), 8.34 (1H, d), 8.32 (1H, d), 7.98 (1H, d), 7.86 (1H, s), 7.80 (1H, d), 7.74 (1H, t), 7.66 (1H, d), 7.31 (1H, dd), 6.98 (1H, d), 2.12 (3H, s).
42.2%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate at 90℃; for 16h; Inert atmosphere;	II.9.2 2. Preparation of N-(5-(9-oxo-10-(3-(trifluoromethyl)phenyl)-9,10-dihydropyrido[3,2-c][1,5]napht hyridin-2-yl)pyridin-2-yl)acetamide General procedure: 2. Preparation of N-(5-(9-oxo-10-(3-(trifluoromethyl)phenyl)-9,10-dihydropyrido[3,2-c][1,5]napht hyridin-2-yl)pyridin-2-yl)acetamide To N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide(225m g, 0.858mmol) were added 2-chloro-10-(3-(trifluoromethyl)phenyl)pyrido[3,2-c][1,5]naphthyridin-9(10H)-o ne(300mg, 0.799mmol), palladium tetrakis(triphenylphosphine)(15mg) and 2N sodium carbonate solution(1.3mL). This system was reacted in a nitrogen-protecting atmosphere at 90 °C for 16hrs. The reaction mixture was cooled to room temperature and filtered. The organic layer was separated out, concentrated in a reduced pressure, dissolved in dichlormethane, successively washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and purified with a silica-gel column chromatography (ethyl acetate) to produce 160 mg of the target compound in a yield of 42.2%. Formula: C25H16F3N5O2 MW: 475.13 MS(M+H): 476.2 1H-NMR(d6-DMSO, 400 MHz):δ 10.65 (1H, s), 9.23 (1H, s), 8.46 (1H, d), 8.37 (1H, d), 8.34 (1H, d), 8.32 (1H, d), 7.98 (1H, d), 7.86 (1H, s), 7.80 (1H, d), 7.74 (1H, t), 7.66 (1H, d), 7.31 (1H, dd), 6.98 (1H, d), 2.12 (3H, s).

Reference： [1]Current Patent Assignee: SIHUAN PHARMACEUTICAL HOLDINGS GROUP LTD. - US2014/93505, 2014, A1 Location in patent: Page/Page column
[2]Current Patent Assignee: SIHUAN PHARMACEUTICAL HOLDINGS GROUP LTD. - EP2719697, 2014, A1 Location in patent: Paragraph 0152; 0155; 0156

21
[ 827614-64-2 ]
[ 904326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
63.1%	With 2-(Dimethylamino)pyridine; acetic anhydride; triethylamine In dichloromethane	9.1 1. 1. Preparation of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300 mg, 1.36 mmol) in dichlormethane (15 mL) were successively added dimethylaminopyridine (17 mg, 0.139 mmol), triethylamine (0.21 mL, 1.50 mmol) and acetic anhydride (153 mg, 1.50 mmol). The resulting mixture was reacted under stirring at room temperature for several hours. Then the reaction mixture was diluted with dichlormethane, and washed with aqueous saturated ammonium chloride solution. The organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated to produce 225 mg of the target compound in a yield of 63.1%.

Reference： [1]Current Patent Assignee: SIHUAN PHARMACEUTICAL HOLDINGS GROUP LTD. - US2014/93505, 2014, A1 Location in patent: Page/Page column

22
[ 904326-87-0 ]
tert-butyl N-(4-bromophenyl)-N-[({4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifiuoromethyl)phenyl}carbamoyl)methyl]carbamate [ No CAS ]
tert-butyl 4-(6-acetamidopyridin-3-yl)phenyl(2-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifiuoromethyl)phenylamino)-2-oxoethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 110℃; for 5h; Inert atmosphere;	11 A solution of tert-butyl N-(4-bromophenyl)-N-[( {4-.[(4-ethylpiperazin- 1-yl)methyl] -3 -(trifiuoromethyl)phenyl } carbamoyl)methyl] carbamate (600 mg, 1.0 mmol),N-[5-(tetramethyl-l,3,2-dioxaborolah-2-yl)pyridin-2-yl]acetamide (262 mg, 1.0 mmol)and K2C03 (272 mg, 2.0 mmol) in dioxane-water (4:1 mL) was degassed with argon. Tothis Pd(dppf)C12.DCM (41 mg, 0.05 mmol) was added and degassed with argon for another 10 mm. The reaction mixture was stirred under argon atmosphere at 110 °C for 5 h. The reaction mixture was cooled to r.t. and diluted with EtOAc. The combined organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentratedunder reduced pressure. The crude compound was purified by column chromatography over neutral alumina using a solvent gradient of 1% MeOH: CHC13 as eluent to afford 550 mg of tert-butyl 4-(6-acetamidopyridin-3 -yl)phenyl(2-(4-((4-ethylpiperazin- 1- yl)methyl)-3 -(trifiuoromethyl)phenylamino)-2-oxoethyl)carbamate (ESI MS: m/z 653.4 [M-H]) which was dissolved in DCM and treated with TFA (6 mL) at room temperaturefor 3 h. The reaction mixture was concentrated under reduced pressure, diluted with water, and washed with EtOAc. The aqueous layer was basified with saturated NaHCO3 solution. Solid separate was filtered, washed with water and dried to afford 280 mg of 2- (4-(6-acetamidopyridin-3 -yl) phenylamino)-N-(4-((4-ethylpiperazin- 1-yl) methyl)-3-

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2014/88519, 2014, A1 Location in patent: Paragraph 000281; 000282

23
[ 904326-87-0 ]
tert-butyl N-(4-bromophenyl)-N-[({4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifiuoromethyl)phenyl}carbamoyl)methyl]carbamate [ No CAS ]
[ 1613168-50-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2014/88519, 2014, A1

24
[ 904326-87-0 ]
tert-butyl 4-(4-(2-((4-bromophenyl)(tert-butoxycarbonyl)amino)acetamido)-2-(trifluoromethyl)benzyl)piperazine-1-carboxylate [ No CAS ]
C₃₇H₄₅F₃N₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 110℃; for 5h; Inert atmosphere;	15 General procedure: A solution of tert-butyl N-(4-bromophenyl)-N-[( {4-.[(4-ethylpiperazin- 1-yl)methyl] -3 -(trifiuoromethyl)phenyl } carbamoyl)methyl] carbamate (600 mg, 1.0 mmol),N-[5-(tetramethyl-l,3,2-dioxaborolah-2-yl)pyridin-2-yl]acetamide (262 mg, 1.0 mmol)and K2C03 (272 mg, 2.0 mmol) in dioxane-water (4:1 mL) was degassed with argon. Tothis Pd(dppf)C12.DCM (41 mg, 0.05 mmol) was added and degassed with argon for another 10 mm. The reaction mixture was stirred under argon atmosphere at 110 °C for 5 h. The reaction mixture was cooled to r.t. and diluted with EtOAc. The combined organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentratedunder reduced pressure. The crude compound was purified by column chromatography over neutral alumina using a solvent gradient of 1% MeOH: CHC13 as eluent to afford 550 mg of tert-butyl 4-(6-acetamidopyridin-3 -yl)phenyl(2-(4-((4-ethylpiperazin- 1- yl)methyl)-3 -(trifiuoromethyl)phenylamino)-2-oxoethyl)carbamate (ESI MS: m/z 653.4 [M-H]) which was dissolved in DCM and treated with TFA (6 mL) at room temperaturefor 3 h. The reaction mixture was concentrated under reduced pressure, diluted with water, and washed with EtOAc. The aqueous layer was basified with saturated NaHCO3 solution. Solid separate was filtered, washed with water and dried to afford 280 mg of 2- (4-(6-acetamidopyridin-3 -yl) phenylamino)-N-(4-((4-ethylpiperazin- 1-yl) methyl)-3-

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2014/88519, 2014, A1 Location in patent: Paragraph 000281; 000282; 000293

25
[ 904326-87-0 ]
tert-butyl 4-(4-(2-((4-bromophenyl)(tert-butoxycarbonyl)amino)acetamido)-2-(trifluoromethyl)benzyl)piperazine-1-carboxylate [ No CAS ]
[ 1613168-67-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2014/88519, 2014, A1

26
[ 904326-87-0 ]
9-chloro-3-methyl-1-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-1(2H)-one [ No CAS ]
N-(5-(3-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimido[5,4-c][1,5]naphthyridin-9-yl)pyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
267mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	2.2 (2) Preparation of N-(5-(3-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyri mido[5,4-c][1,5]naphthyridin-9-yl)pyridin-2-yl)acetamide 9-chloro-3-methyl-1-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrimido [5,4-c][1,5]naphthyridin-2(1H)-one (314mg, 0.80mmol), tetrakis(triphenylphosphine) palladium (15mg, 0.013mmol) and 2N aqueous sodium carbonate solution (1.3mL) were added sequentially to a solution of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (225mg, 0.858mmol) in 1,4-dioxane (15mL), and reacted under nitrogen at 90 °C for 16 h, cooled to room temperature, filtered, the organic layer was concentrated under reduced pressure, dissolved in 50mL of dichloromethane, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (ethyl acetate) to give 267mg of the product. Molecular formula: C25H19F3N6O2; Molecular weight: 492.1; Mass spectrum (M+H): 493.2 1H-NMR(d6-DMSO, 400 MHz): δ 10.64 (1H, s), 8.81 (1H, s), 8.41 (1H, d), 8.37 (1H, d), 8.25 (1H, d), 7.98 (1H, d), 7.82 (1H, s), 7.67-7.62 (1H, m), 7.61-7.52 (2H, m), 7.37 (1H, dd), 4.79 (2H, s), 3.01 (3H, s), 2.10 (3H, s)
267 mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	2.2 (2) Preparation of N-(5-(3-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimido[5,4-c][1,5]naphthyridin-9-yl)pyridin-2-yl)acetamide 9-chloro-3-methyl-1-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-2(1H)-one (314 mg, 0.80 mmol), tetrakis(triphenylphosphine) palladium (15 mg, 0.013 mmol) and 2N aqueous sodium carbonate solution (1.3 mL) were added sequentially to a solution of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (225 mg, 0.858 mmol) in 1,4-dioxane (15 mL), and reacted under nitrogen at 90° C. for 16 h, cooled to room temperature, filtered, the organic layer was concentrated under reduced pressure, dissolved in 50 mL of dichloromethane, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (ethyl acetate) to give 267 mg of the product. Molecular formula: C25H19F3N6O2; Molecular weight: 492.1; Mass spectrum (M+H): 493.2 1H-NMR (d6-DMSO, 400 MHz): δ 10.64 (1H, s), 8.81 (1H, s), 8.41 (1H, d), 8.37 (1H, d), 8.25 (1H, d), 7.98 (1H, d), 7.82 (1H, s), 7.67-7.62 (1H, m), 7.61-7.52 (2H, m), 7.37 (1H, dd), 4.79 (2H, s), 3.01 (3H, s), 2.10 (3H, s)

Reference： [1]Current Patent Assignee: SIHUAN PHARMACEUTICAL HOLDINGS GROUP LTD. - EP2781520, 2014, A1 Location in patent: Paragraph 0123; 0126 - 0129
[2]Current Patent Assignee: SIHUAN PHARMACEUTICAL HOLDINGS GROUP LTD. - US2015/166539, 2015, A1 Location in patent: Paragraph 0263; 0266; 0267; 0268; 0269

27
[ 2527-99-3 ]
[ 904326-87-0 ]
methyl 5-(2-acetamidopyridin-4-yl)furan-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 3h; Inert atmosphere;	1 Step 1: Preparation of methyl 5-(2-acetamidopyridin-4-yl)furan-2-carboxylate General procedure: Step 1: Preparation of methyl 5-(2-acetamidopyridin-4-yl)furan-2-carboxylate Using the same reaction conditions as described in step 7 of example 1, N-(5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (1.91g, 7.317 mmol) was coupled with methyl 5-bromofuran-2-carboxylate (lg, 4.87 mmol) using sodium carbonate (1.54g, 14.61 mmol) and Pd(dppf)Cl2 (178mg, 0.243 mmol) in 1 ,2-dimethoxyethane/water (20/4mL) at 80°C for 3h to get the crude product. The resultant crude was purified by flash chromatography using 35% ethyl acetate in hexane as eluent to obtain the title compound (451mg, 35.6%). LCMS: m/z: 261.1 (M+l)+.
35.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 3h; Sealed tube; Inert atmosphere;	22.1 Step 1: Preparation of methyl5-(2-acetamidopyridin-4-yl)furan-2-carboxylate Using the same reaction conditions as described in step 7 of example 1, N-(5-(4,4,5,5-tetramethyl-1 ,3,2-dioxa- borolan-2-yl)pyridin-2-yl)acetamide (1.91 g, 7.317 mmol) was coupled with methyl 5-bromothran-2-carboxylate (1 g, 4.87 mmol) using sodium carbonate (1.54 g, 14.61 mmol) and Pd(dppf)C12 (178 mg, 0.243 mmol) in 1,2-dimethoxy- ethane/water (20/4 mE) at 80° C. for 3 h to get the crude product. The resultant crude was purified by flash chromatography using 35% ethyl acetate in hexane as eluent to obtain the title compound (451 mg, 35.6%). ECMS: mlz:261.1 (M+1). To a sealed tube 6-bromo-N-(2-morpholinooxazolo [4,5-b]pyridin-6-yl)picolinamide (350 mg, 0.866 mmol), tert-butyl (5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl) pyridin-2-yl)carbamate (360 mg, 1.126 mmol) (intermediate 1), sodium carbonate (275 mg, 2.598 mmol) in 1,2-dime- thoxyethane (10 mL) and water (2 mL) were added. The reaction mixture was purged with argon for 10 mm, added Pd(PPh3)2C12 (31 mg, 0.043 mmol) and heated at 95° C. overnight. The solvent was distilled out. The resultant crude was purified by 60-120 silica gel column chromatography using 5% methanol in DCM as eluent to obtain the title compound (300 mg, 67.11%).

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2015/104688, 2015, A1 Location in patent: Page/Page column 35
[2]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2016/340366, 2016, A1 Location in patent: Paragraph 0199; 0216

28
[ 904326-87-0 ]
trifluoro-methanesulfonic acid 2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-methyl-vinylester [ No CAS ]
C₂₃H₂₆N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water for 0.75h; Reflux;	93; 94 Example 93 Preparation of Compound No. 111 Example 93 Preparation of Compound No. 111 (1306) To a solution of [(E,Z)-1-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)prop-1-en-2-yl trifluoromethanesulfonate] (100 mg), potassium carbonate (36 mg), and 2-acetamidopyridine-5-boronic acid pinacol ester (135 mg) in DME-water (4:2 mL) was added Pd(PPh3)4 (15 mg) and the reaction mixture was heated to reflux for 45 min. The reaction mixture was cooled to RT, and the solvent was removed under reduced pressure. The residue was diluted with water and extracted with EtOAc. The organic layer was washed with brine, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.91 (s, 1H), 7.68 (d, 1H), 7.58 (d, 1H), 7.21 (s, 1H), 7.10 (d, 1H), 6.98 (d, 1H), 6.91 (s, 1H), 4.61 (d, 1H), 4.30 (d, 1H), 3.71 (m, 1H), 3.40 (m, 1H), 3.07 (s, 3H), 2.90 (m, 2H), 2.38 (m, 6H), 2.16 (s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2015/266884, 2015, A1 Location in patent: Paragraph 1306; 1307

29
[ 904326-87-0 ]
5-(2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile [ No CAS ]
N-(5-(4-(3-cyano-4-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)pyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In 1,4-dioxane; water at 85℃; for 0.5h;	236.1 Step 1 : Preparation of N-(5-(4-(3-cyano-4-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)- 1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridin-2-yl)pyridin-2-yl)acetamide: A mixture of 5-(2-iodo-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridin-4-yl)-2-((tetrahydro-2H-pyran-4- yl)oxy)benzonitrile (0.28 g, 0.47 mmol), tert-butyl 3-(4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazol-1-yl)azetidine-1-carboxylate (Sigma Aldrich, 0.15 g, 0.57 mmol), cesium carbonate (0.39 g, 1.2 mmol), and bis(triphenylphosphine)palladium(ll) dichloride (0.02 g, 0.03 mmol) in 1 ,4-dioxanes (3 mL) and water (1 mL), was heated for 30 minutes on an 85 °C block. After cooling to room temperature, the mixture was purified via flash chromatography on silica gel to give the desired material. LCMS-ESI+ (m/z): [M+H]+ calcd for C32H28N5O5S: 594.2; found: 594.5

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - WO2015/187684, 2015, A1 Location in patent: Page/Page column 267-268

30
[ 904326-87-0 ]
8-bromo-1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one [ No CAS ]
N-(5-(2-oxo-1-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)pyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Inert atmosphere; Microwave irradiation;	General Procedure for Suzuki Coupling. 8-(6-Aminopyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one(11) General procedure: Under an N2 atmosphere, a solution of S3 (30 mg, 0.073 mmol) and 2-aminopyridine-5-boronic acid pinacol ester (11 mg, 0.081 mmol) in DMF (1.5 mL) and saturated aqueous NaHCO3 (0.5 mL) was treated with Pd(PPh3)4 (5mg, 3.7 µmol). The reaction mixture was heated under microwave irradiation at 120°C for 20 minutes. The resulting mixture was diluted with water, and extracted with dichloromethane. The organics were combined, dried, filtered, and concentrated. Purification via preparative reverse phase HPLC afforded 11 as an off-white solid (11 mg, 26%).

Reference： [1]Patel, Paresma R.; Sun, Wei; Kim, Myunghoon; Huang, Xiuli; Sanderson, Philip E.; Tanaka, Takeshi Q.; McKew, John C.; Simeonov, Anton; Williamson, Kim C.; Zheng, Wei; Huang, Wenwei [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 12, p. 2907 - 2911]

31
[ 904326-87-0 ]
8-bromo-3-methyl-1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one [ No CAS ]
N-(5-(3-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)pyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Inert atmosphere; Microwave irradiation;	General Procedure for Suzuki Coupling. 8-(6-Aminopyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one(11) General procedure: Under an N2 atmosphere, a solution of S3 (30 mg, 0.073 mmol) and 2-aminopyridine-5-boronic acid pinacol ester (11 mg, 0.081 mmol) in DMF (1.5 mL) and saturated aqueous NaHCO3 (0.5 mL) was treated with Pd(PPh3)4 (5mg, 3.7 µmol). The reaction mixture was heated under microwave irradiation at 120°C for 20 minutes. The resulting mixture was diluted with water, and extracted with dichloromethane. The organics were combined, dried, filtered, and concentrated. Purification via preparative reverse phase HPLC afforded 11 as an off-white solid (11 mg, 26%).

32
[ 904326-87-0 ]
1-(3-(6-bromo-7-(difluoromethyl)-3,4-dihydroquinolin-1(2H)-yl)-1-(tetrahydro-2H-pyran-4-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone [ No CAS ]
N-[5-[1-(5-acetyl-1-tetrahydropyran-4-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-7-(difluoromethyl)-3,4-dihydro-2H-quinolin-6-yl]-2-pyridyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); sodium carbonate; XPhos In tetrahydrofuran; water at 60℃; for 16h; Inert atmosphere;	310 N- [5-ji -(5-acetyl-1-tetrahydropyran-4-yI-6,7-dihydro-4H-pyrazolo 14,3-cl pyridin-3-yl)-7- (difluoromethyI)-3,4-dihydro-2H-quinolin-6-yI-2-pyridyIJacctamide To a solution of 1 -(3 -(6-bromo-7-(difluoromethyl)-3 ,4-dihydroquinolin- I(211)-yl)-I - (tetrahydro-2H-pyran-4-yl)-6,7-dihydro- IH-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone (Intermediate F, 210 mg, 0.41 mmol) in THF (5 mL) and water (1 mE) was added N-(5- (4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (130 mg, 0.49 mmol), chloro(2-dicyclohexylphosphino-2’,4’,6’-tri-i-propyl- 1,1 ‘-biphenyl)(2’-amino- 1,1 -bipheny1-2-yl) palladium (II) (32 mg, 0.04 mmol), 2-(dicyclohcxylphosphino)-2’,4’,6’- triisopropylbiphenyl (20 mg, 0.04 mmol) and Na2CO3 (130 mg, 1.23 mmol). The mixture was heated to 60 °C for 16 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was concentrated in vacuo. The crude residue was purified by reverse phase chromatography (acetonitrile 30-60% / 0.05% N1140l-l in water) to give thetitle compound (131 mg, 56%) as a white solid. ‘H NMR (400 MHz, DMSO-d6) 8.29 - 8.19(m, 2H), 8.05 - 8.03 (m, 111), 7.69 - 7.66 (m, 1H), 6.99 - 6.95 (m, IH), 6.90 (s, IH), 6.53 -6.23 (m, IH), 4.28 (s, IH), 4.16 -4.13 (m, 411), 3.93 - 3.91 (m, 111), 3.77 - 3.72 (m, 3H), 3,563.50 (m, 211), 2.92 - 2.88 (m, 311), 2.84 - 2.77 (m, IH), 2.33 - 2.30 (m, 511), 2.18 - 2.07 (m,4H), 1.90 - 1.87 (m, 2H). LCMS MZ (M+H) 565.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; MORPHOSYS AG; WUXI APPTEC CO., LTD. - WO2016/86200, 2016, A1 Location in patent: Page/Page column 442

33
[ 904326-87-0 ]
N-[4-methyl-3-(4-bromothiazol-2-ylamino)phenyl]-4-[(4-methylpiperazinyl)methyl]benzoylamine [ No CAS ]
N-{4-methyl-3-[4-(6-acetylaminopyridin-3-yl)thiazol-2-ylamino]phenyl}-4-[(4-methylpiperazinyl)methyl]benzenecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30 mg	With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In 1,4-dioxane; water at 150℃; for 1.5h; Inert atmosphere; Microwave irradiation;	5.F the preparation of N- {4- methyl-3- [4- (6-acetylamino-pyridin-3-yl) thiazole-2-amino]phenyl} - 4 - [(4-methyl piperazin yl) methyl] benzamide theStep C compound (0.2 mmol), the compound of Step E (0.24 mmol), cesiumcarbonate (0.6 mmol) and Bis triphenylphosphine palladium dichloride (0.01mmol) dissolved in a mixed solution of Dioxane and water (5/2, 3.5 mL). Understirring, continuously for 5 minutes replaced with nitrogen. The reactionsystem was placed in a microwave reactor, at 150 ° C stirred for 1.5 hours.Cooling to room temperature, the 20 ml of water was added and the mixed solution was extracted with dichloromethane.The extract was dried over anhydrous sodium sulfate then the solvent was concentratedand Separation by column chromatography (Dichloromethane / methanol = 10:1)togive 30 mg of the title compound.

Reference： [1]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED; SHOUYAO HOLDINGS BEIJING CO LTD - CN103130792, 2016, B Location in patent: Paragraph 0193-0194; 0210-0212

34
[ 1072-97-5 ]
[ 904326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane / 20 °C / Industrial scale 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 100 °C / Inert atmosphere; Industrial scale
	Multi-step reaction with 2 steps 1: acetone / 48 h 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: LIANHUA CHEMISTRY DALIAN - CN103601745, 2017, B
[2]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED; SHOUYAO HOLDINGS BEIJING CO LTD - CN103130792, 2016, B

35
[ 7169-97-3 ]
[ 25015-63-8 ]
[ 904326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
0.6 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 150℃; for 2h;Inert atmosphere; Microwave irradiation;	TheNu- (5- bromo-pyridin-2-yl) acetamide (0.7 g, 3.3 mmol), pinacol boronic ester(0.91 g, 3.6 mmol), Potassium acetate (9.9 mmol) and 1,1'-Bis(diphenylphosphino)ferrocenepalladium(II) dichloride(0.2mmol) mixed in N, N- dimethylformamide (5 ml), andrepeatedly replaced 3 times with nitrogen . The system placed in a microwavereactor and at 150 C stirred for 2 hours. Cooled to room temperature, thesolvent was removed under reduced pressure and the obtained crude product waswashed with petroleum ether repeatedly. After washing with petroleum ether and concentrationto give 0.6 g of the title compound.

Reference： [1]Patent: CN103130792,2016,B .Location in patent: Paragraph 0207-0209

36
[ 26218-75-7 ]
[ 904326-87-0 ]
methyl 2’-acetamido-[2,4’-bipyridine]-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.5%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 110℃; for 12h;	43.2 Step 2: Synthesis ofmethyl 2’-acetamido-[2,4’-bipyridine]-6-carboxylate To a stined solution of N-(5-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2- yl)acetamide (2.78g, 13.8Smmol) in 1,2-dimethoxyethane/water (20I5mL) were added methyl 6- bromopicolinate(2.5g, 11 .Smmol), sodium carbonate (2.45g, 23. immol) and Pd(DPPF)C12 (0.423g, 0.Smmol), stined at 110°C for 12h. The reaction mixture was filtered and the filtrate was concentrated to get the crude product which was purified by using 60-120 silica gel columnchromatography, 50% ethyl acetate in hexane as eluent to obtain the title compound (1.lg,35.5%). LCMS: mlz = 272.0 (M+1).

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2017/9798, 2017, A1 Location in patent: Page/Page column 92

37
[ 904326-87-0 ]
N-(5-bromo-2-(3,4-dimethylpiperazin-1-yl)-4-fluorophenyl)-4-(trifluoromethyl)-6-(2-(trimethylsilyl)ethoxy)nicotinamide [ No CAS ]
N-[5-(6-acetamidopyridin-3-yl)-4-fluoro-2-[rac-(3R)-3,4-dimethylpiperazin-1-yl]phenyl]-6-oxo-4-(trifluoromethyl)-1H-pyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide; N-(5-bromo-2-(3,4-dimethylpiperazin-1-yl)-4-fluorophenyl)-4-(trifluoromethyl)-6-(2-(trimethylsilyl)ethoxy)nicotinamide With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 110℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: With trifluoroacetic acid In dichloromethane for 1h;	196.8 N-[5-( 6-acetamidopyridin-3-yl)-4-fluoro-2-[(3R)-3, 4-dimethylpiperazin-1- yl]phenyl]-6-oxo-4-(trifluoromethyl)-lH-pyridine-3-carboxamide In a 5 mL microwave vial 2-acetamidopyridine-5-boronic acid, pinacol ester (0.034 g, 0.131 mmol), (S)-N-(5-bromo-2-(3,4-dimethylpiperazin-1-yl)-4- fluorophenyl)-4-(trifluoromethyl)-6-(2-(trimethylsilyl)ethoxy Nicotinamide (0.05183 g, 0.088 mmol), bis(di-tert-butyl(4- dimethylaminophenyl)phosphine)dichloropalladium(II) (6.20 mg, 8.76 μηιο) and potassium phosphate tribasic reagent grade (0.037 g, 0.175 mmol) were dissolved in water (0.175 ml) / 1,4-dioxane (1.577 ml) (9 : 1 mixture) to give a white suspension. The suspension was stirred for 5 min, degassed, purged with N2, and microwaved for 60 min at 110 °C. The solvent was evaporated and 15 mL of CH2C12 were added. The suspension was sonicated and extracted from water (15 mL). The solvent was evaporated in vacuo yielding the crude product that was purified by flash column chromatography on silica gel (0-100%, 89% CH2C12, 10% MeOH, 1% NH4Ac/CH2Cl2) to afford the protected intermediate. The product was dissolved in 2 mL of DCM and trifiuoroacetic acid (0.101 ml, 1.314 mmol) was added. The purple solution was stirred for 1 h and the solvent was evaporated. The residue was purified using a cation exchange column eluting with MeOH:NH4OH. 11H NMR (500 MHz, MeOD-d4) δ 8.37 (s, 1H), 8.08 (d, J= 8.6 Hz, 1H), 7.87 (s, 1H), 7.84 (d, J= 7.7 Hz, 2H), 7.00 (d, J= 12.1 Hz, 1H), 6.81 (s, 1H), 3.02 (dq, J = 11.6, 2.0 Hz, 1H), 2.97 (dt, J = 11.6, 2.2 Hz, 1H), 2.87 - 2.80 (m, 2H), 2.50 - 2.42 (m, 2H), 2.32 (ddd, J = 9.4, 6.4, 2.7 Hz, 1H), 2.27 (s, 3H), 2.10 (s, 3H), 1.03 (d, J= 6.3 Hz, 3H); LCMS [M+l]+ = 547.28.

Reference： [1]Current Patent Assignee: PROPELLON THERAPEUTICS - WO2017/147700, 2017, A1 Location in patent: Paragraph 00488

38
[ 904326-87-0 ]
2-bromo-4-propyloxazole [ No CAS ]
N-(5-(4-propyloxazol-2-yl)pyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; water at 90℃;

Reference： [1]Solomin, Vitalii V.; Radchenko, Dmytro S.; Slobodyanyuk, Evgeniy Y.; Geraschenko, Oleksandr V.; Vashchenko, Bohdan V.; Grygorenko, Oleksandr O. [European Journal of Organic Chemistry, 2019, vol. 2019, # 18, p. 2884 - 2898]

39
[ 142404-84-0 ]
[ 73183-34-3 ]
[ 904326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
82.96%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃; for 3h; Inert atmosphere;	1 Step 1 To a solution of N-(5-bromo-6-methylpyridin-2-yl)acetamide (300.0 mg, 1.31mol) in dioxane (3mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (399.07 mg, 1.57mol) , potassium acetate (192.79 mg, 1.96 mol) and Pd(dppf)Cl2 (lOmg) . The mixture was stirred at 120°C for 3h under the N2. LCMS showed the reaction was completed. Water was added and extracted with EtOAc (3*10mL). The organic layer was dried by Na2SO4 and filtration. The filtrate was concentrated to afford crude product. The crude product was purification by silica gel chromatography PE: EtOAc (5: 1) to afford N-(5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (300 mg , 82.96%) as a white solid.

Reference： [1]Current Patent Assignee: NANJING ZHENGXIANG PHARMACEUTICALS; HANGZHOU ZHENGXIANG PHARMACEUTICALS - WO2020/210379, 2020, A1 Location in patent: Paragraph 0102

40
[ 904326-87-0 ]
(S)-5-bromo-2-(1-cyclopropylethyl)-7-(dimethylphosphoryl)isoindolin-1-one [ No CAS ]
(S)-N-(5-(2-(1-cyclopropylethyl)-7-(dimethylphosphoryl)-1-oxoisoindolin-5-yl)pyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; for 8h; Inert atmosphere;	2 Step 2 To a solution of N-(6-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-yl)acetamide (50.0 mg, 181.1 umol) in dioxane/H2O (2 : 0.5mL), was added (S)-5- bromo-2-(l-cyclopropylethyl)-7-(dimethylphosphoryl)isoindolin-l-one (77.39 mg, 0.22 mmol) , Na2CO3 (38.38 mg, 0.36 mmol) and Pd(dppf)Cl2 (5mg). The mixture was stirred at 85 °C for 8h under N2. LCMS showed the reaction was completed. Water was added and exacted with EtOAc (3*10 mL). The organic layer was dried by Na2SO4 and filtration. The filtrate was concentrated to afford crude product. The crude product was purification by HPLC (AcOH in water, ACM) to afford (S)-N-(5-(2-(l-cyclopropylethyl)-7-(dimethylphosphoryl)-l-oxoisoindolin-5-yl)pyridin-2- yl)acetamide (19.08 mg 26%) as white solid. LC-MS (ESI) [M+H]+ 426.3, 1H NMR (400 MHz, DMSO) d 10.61 (s, 1H), 8.13 (s, 1H), 8.04 (d, J = 8.4 Hz, 1H), 7.99 (d, J = 12.1 Hz, 1H), 7.85 (s, 1H), 7.67 (d, J = 8.5 Hz, 1H), 4.67 (s, 2H), 3.63 (s, 1H), 2.40 (s, 3H), 2.11 (s, 3H), 1.88 (d, J = 14.3 Hz, 6H), 1.31 (d, J = 6.8 Hz, 3H), 1.18 - 1.10 (m, 1H), 0.59 (s, 1H), 0.41 (dd, J = 11.4, 5.4 Hz, 2H), 0.26 (d, J = 5.4 Hz, 1H).

Reference： [1]Current Patent Assignee: NANJING ZHENGXIANG PHARMACEUTICALS; HANGZHOU ZHENGXIANG PHARMACEUTICALS - WO2020/210379, 2020, A1 Location in patent: Paragraph 0102-0103

41
[ 904326-87-0 ]
(S)-methyl 2-(3-(4-bromophenylthio)propanamido)-3-methylbutanoate [ No CAS ]
(2S)-2-(3-[4-(6-acetamidopyridin-3-yl)phenyl]sulfanyl}propanamido)-3-methylbutanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene for 18h; Reflux; Inert atmosphere;	4.1.5. General procedure for Suzuki synthesis of valine derivatives58e66 General procedure: To a solution of compound 56 (1eq, 0.2 mmol), boronic acid orester derivative (1.5 eq, 0.3 mmol) and Pd[P(Ph3)]4 (5 mol%) in amixture toluene/ethanol (2/0.5 mL) was added an aqueous solutionof Na2CO3 (2 eq, 0.4 mmol, 0.5 mL). The resulting mixture wasrefluxed under argon atmosphere during 18 h, cooled and thenconcentrated. To the resulting residue was added dropwise 1 N HClsolution 4 C until pH 1, the aqueous layer was extracted twice withethyl acetate. The combined organic layers were washed once withwater, once with brine, dried over Na2SO4, and evaporated undervacuum. Crude was purified by column chromatography elutingwith dichloromethane-methanol (98:2 to 80:20).

Reference： [1]Garcia, Manon; Hoffer, Laurent; Leblanc, Raphaël; Benmansour, Fatiha; Feracci, Mikael; Derviaux, Carine; Egea-Jimenez, Antonio Luis; Roche, Philippe; Zimmermann, Pascale; Morelli, Xavier; Barral, Karine [European Journal of Medicinal Chemistry, 2021, vol. 223]

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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. 904326-87-0 ]

Quality Control of [ 904326-87-0 ]

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[ 904326-87-0 ] Synthesis Path-Downstream 1~41

Related Functional Groups of [ 904326-87-0 ]

Organoboron

Amides

Esters

Amines

Related Parent Nucleus of [ 904326-87-0 ]

Pyridines

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[ 904326-87-0 ]

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[ 904326-87-0 ]