Name: 945863-21-8|N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide|98%
Brand: Ambeed
SKU: A248099
Rating: 91 (29 reviews)

1
N-(4-bromo-2-fluorophenyl)-N'-(cis-4-hydroxycyclohexyl)-N,N'-dimethylurea [ No CAS ]
[ 945863-21-8 ]
5-(3-fluoro-4-[[(cis-4-hydroxycyclohexyl)(methyl)amino]carbonyl(methyl)amino]phenyl)-N-methylpyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 120℃; for 4h;	Example 75-3-Fluoro-4-[[(cis-4-hydroxycyclohexyl)(methyl)amino]carbonyl(methyl)amino]phenyl-N-methylpyridine-2-carboxamide; A mixture of N-(4-bromo-2-fluorophenyl)-N'-(cis-4-hydroxycyclohexyl)-N,N'- dimethylurea (10.0 mg, 0.0000278 mol), N-methyl-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridine-2-carboxamide (10.9 mg, 0.0000418 mol) and potassium carbonate (11.5 mg, 0.0000835 mol) in N,N-dimethylformamide (0.223 mL, 0.00288 mol) was degassed with nitrogen for 5 min. After addition of [l,l'-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane (1 : 1) (3.41 mg, 4.18E-6 mol), the resulting mixture was heated at 120 0C for 4 h. The reaction mixture was diluted with acetonitrile and water, filtered through a 0.3 U membrane. The filtration was applied on RP-HPLC to generate the desired product (5 mg, 40%). LCMS (M+H) 415.2.

Reference： [1]Patent: WO2007/130898,2007,A1 .Location in patent: Page/Page column 47

2
1-(4-bromo-2-fluorophenyl)piperidin-3-yl-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
[ 945863-21-8 ]
1-{2-fluoro-4-6-[(methylamino)carbonyl]pyridin-3-ylphenyl}piperidin-3-yI-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxyIate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.5%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 120℃; for 4.08333h;	A mixture of l-(4~brorno-2-fluorophenyl)piperidin~3-yl-3-hydroxy-8- azabicyclo[3.2.1]octane-8-carboxylate (25.0 mg, 0.0000585 mol), N-methyl-5-(4,4,5,5-tetramethyI- l,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (23.0 mg, 0.0000878 mol) and potassium carbonate (24.2 mg, 0.000176 mol) in N,N-dimethylformamide (0.50 mL, 0.0064 mol) was purged with nitrogen for 5 min. After [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane (1 :1) (7.17 mg, 8.78E-6 mol) was added, the resulting mixture was heated at 120 0C for 4 h. The reaction mixture was diluted with AcCN and water, filtered through a 0.3 U membrane. The filtration was applied on RP-HPLC to generate the desired product (21 mg, 74.5%). LCMS (M+H) 483.2. The product was believed to have 3S stereochemistry and 3-endo configuration based on the starting materials.

Reference： [1]Patent: WO2007/89683,2007,A1 .Location in patent: Page/Page column 67

3
1'-[(4-bromo-2-fluorophenyl)(methoxy)acetyl]-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one [ No CAS ]
[ 945863-21-8 ]
5-(3-fluoro-4-1-methoxy-2-oxo-2-[3-oxo-1'H,3H-spiro[2-benzofuran-1,3'-pyrrolidin]-1'-yl]ethylphenyl)-N-methylpyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.54%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 4.08333h;	A mixture of 1'-[(4-bromo-2-fluorophenyl)(methoxy)acetyl]-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one (20.0 mg, 0.0000460 mol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong> (18.1 mg, 0.0000691 mol) and potassium carbonate (19.1 mg, 0.000138 mol) in N,N-dimethylformamide (0.39 mL) was purged with nitrogen for 5 min. After an addition of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II),complex with dichloromethane (1:1) (5.64 mg, 6.91E-6 mol), the resulting mixture was heated at 100 C. for 4 h. The reaction mixture was diluted with AcCN and water, filtered through a 0.3 U membrane. The filtrate was applied on RP-HPLC to yield the desired product (15 mg, 66.54%). The product was believed to be in the form of a trifluoroacetic acid salt. LCMS (M+H) 490.1.

Reference： [1]Patent: US2007/213311,2007,A1 .Location in patent: Page/Page column 26

4
2-(4-bromo-2-fluorophenyl)-1-oxo-1-(1,3,3-trimethyl-6-azabicyclo[3.2.1]oct-6yl)propan-2-ol [ No CAS ]
[ 945863-21-8 ]
5-(3-fluoro-4-[1-hydroxy-1-methyl-2-oxo-2-(1,3,3-trimethyl-6-azabicyclo[3.2.1]oct-6-yl)ethyl]phenyl)-N-methylpyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.77%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 120℃; for 4.08333h;	A mixture of 2-(4-bromo-2-fluorophenyl)-1-oxo-1-(1,3,3-trimethyl-6-azabicyclo[3.2.1]oct-6-yl)propan-2-ol (25.0 mg, 0.0000628 mol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong> (24.7 mg, 0.0000941 mol) and potassium carbonate (26.0 mg, 0.000188 mol) in N,N-dimethylformamide (0.502 mL, 0.00649 mol) was degassed with nitrogen for 5 min. To the mixture was added [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (7.69 mg, 9.41E-6 mol). The resulting mixture was heated at 120 C. for 4 h. The reaction mixture was diluted with AcCN and water and filtered through a 0.3 U membrane. The filtration was applied on RP-HPLC to generate the desired product (21 mg, 73.77%). The product was believed to be in the form of a trifluoroacetic acid salt. LCMS (M+H) 454.2.

Reference： [1]Patent: US2007/213311,2007,A1 .Location in patent: Page/Page column 31

5
1'-[2-(4-bromophenyl)propanoyl]-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one [ No CAS ]
[ 945863-21-8 ]
N-methyl-5-(4-1-methyl-2-oxo-2-[3-oxo-1'H,3H-spiro[2-benzofuran-1,3'-pyrrolidin]-1'-yl]ethylphenyl)pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.37%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 120℃; for 4.08333h;	A mixture of 1'-[2-(4-bromophenyl)propanoyl]-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one (30.0 mg, 0.0000750 mol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong> (29.5 mg, 0.000112 mol) and potassium carbonate (31.1 mg, 0.000225 mol) in N,N-dimethylformamide (0.600 mL, 0.00775 mol) was purged with nitrogen for 5 min. After an addition of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (9.18 mg, 0.0000112 mol), the resulting mixture was heated at 120 C. for 4 h. The reaction mixture was diluted with AcCN and water, filtered through a 0.3 U membrane. The filtrate was applied on RP-HPLC to generate the desired product (23 mg, 67.37%). The product was believed to be in the form of a trifluoroacetic acid salt. LCMS (M+H) 456.2.

Reference： [1]Patent: US2007/213311,2007,A1 .Location in patent: Page/Page column 29

6
6-[(4-bromo-2-fluorophenyl)(fluoro)acetyl]-1,3,3-trimethyl-6-azabicyclo[3.2.1]octane [ No CAS ]
[ 945863-21-8 ]
5-(3-fluoro-4-[1-fluoro-2-oxo-2-(1,3,3-trimethyl-6-azabicyclo[3.2.1]oct-6-yl)ethyl]phenyl)-N-methylpyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.99%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 120℃; for 4.08333h;	A mixture of 6-[(4-bromo-2-fluorophenyl)(fluoro)acetyl]-1,3,3-trimethyl-6-azabicyclo[3.2.1]octane (25.0 mg, 0.0000647 mol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong> (25.4 mg, 0.0000971 mol) and potassium carbonate (26.8 mg, 0.000194 mol) in N,N-dimethylformamide (0.518 mL, 0.00669 mol) was degassed with nitrogen for 5 min. To the mixture was added [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (7.93 mg, 9.71E-6 mol). The resulting mixture was then heated at 120 C. for 4 h. The reaction mixture was diluted with acetonitrile and water and then filtered through a 0.3 U membrane. The filtration was applied on RP-HPLC to generate the desired product (18 mg, 62.99%). The product was believed to be in the form of a trifluoroacetic acid salt. LCMS (M+H) 442.2.

Reference： [1]Patent: US2007/213311,2007,A1 .Location in patent: Page/Page column 30-31

7
4-(4-bromo-2-methylphenyl)-4-hydroxy-N-(cis-4-hydroxycyclohexyl)cyclohexanecarboxamide [ No CAS ]
[ 945863-21-8 ]
5-[4-(1-hydroxy-4-[(cis-4-hydroxycyclohexyl)amino]carbonyl}cyclohexyl)-3-methylphenyl]-N-methylpyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 2h;	A mixture of <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong> (14 mg, 0.055 mmol), tetrakis(triphenylphosphine)palladium(0) (1.6 mg, 0.0014 mmol), K3PO4 (23 mg, 0.11 mmol), and 4-(4-bromo-2-methylphenyl)-4-hydroxy-N-(cis-4-hydroxycyclohexyl)-cyclohexane-carboxamide (15.0 mg, 0.0366 mmol) in 1,4-dioxane (0.3 mL) and water (0.3 mL) was stirred at 120 C. for 2 h. After cooling, the mixture was filtered. The filtrate was diluted with methanol (1.3 mL) and purified by prep-HPLC (pH=2 conditions) to afford 5-[4-(1-hydroxy-4-[(cis-4-hydroxycyclohexyl)-amino]-carbonyl}cyclohexyl)-3-methylphenyl]-N-methylpyridine-2-carboxamid (15 mg). LCMS: (M+H)+=466.2.

Reference： [1]Patent: US2007/208001,2007,A1 .Location in patent: Page/Page column 43-44

8
[ 945863-21-8 ]
[ 1029715-51-2 ]
[ 1029713-58-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 120℃;	To a solution of 6-{l-[6-(4-bromo-3-fluorophenyl)imidazo[l,2-a]pyrimidin-3- yl]cyclopropyl}quinoline (20 mg, 0.04 mmol) in 1,4-dioxane (1 mL) was added N-methyl-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (17 mg, 0.065 mmol), tetrakis(triphenylphosphine)palladium (3 mg, 0.003 mmol), and potassium phosphate (28 mg, 0.13 mol). The mixture was heated at 120 0C overnight. After cooling to RT, the solution was purified by RP-HPLC (pH 2) to afford the desired compound as a TFA salt. LCMS: (M+H) = 515.0.

Reference： [1]Patent: WO2008/64157,2008,A1 .Location in patent: Page/Page column 89

9
[ 945863-21-8 ]
[ 1029715-74-9 ]
[ 1029713-67-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; ethanol; water; at 120℃; for 1h;Sealed tube;	To a solution of 6-{l-[2-(4-bromophenyl)imidazo[l,2-b][l,2,4]triazin-7- yl]cyclopropyl}quinoline (10.0 mg, 0.0226 mmol) in 1,4-dioxane (1 mL), EtOH (0.2 mL) and water (0.2 mL) was added N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2- <n="95"/>carboxamide (12 mg, 0.045 mmol), cesium carbonate (15 mg, 0.045 mmol), and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II),complex with dichloromethane (1 :1) (1.8 mg, 0.0023 mmol). The reaction vessel was purged with N2 and then heated in a sealed tube at 120 0C for 1 h. LCMS and HPLC data indicated that the reaction was complete. The mixture was purified by RP- HPLC (pH 2) to give the desired product as a TFA salt. LCMS: (M+H) = 498.1.

Reference： [1]Patent: WO2008/64157,2008,A1 .Location in patent: Page/Page column 93-94

10
[ 945863-21-8 ]
[ 1093751-57-5 ]
[ 1093751-40-6 ]

Yield	Reaction Conditions	Operation in experiment
59.3%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 24h;	Step 8: 5-3-fluoro-4-[(5S)-2-(cis-4-hydroxycyclohexyl)-1-oxo-2,7-diazaspiro[4.5]dec-7-yl]phenyl-N-methylpyridine-2-carboxamide Potassium phosphate (637 mg, 0.00300 mol) in water (3.00 mL) was added to a mixture of (5S)-7-(4-bromo-2-fluorophenyl)-2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (425 mg, 0.00100 mol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong> (Frontier Inc., cat #: M10074) (393 mg, 0.00150 mol) and tetrakis(triphenylphosphine)palladium (Aldrich, cat #: 216666) (35 mg, 0.000030 mol) in 1,4-dioxane (3.00 mL). The resulting mixture was heated at 120 C. for 24 h. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column eluding with 5% methanol in DCM to yield the desired product (285 mg, 59.3%). LC/MS m/e 481.2 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): 8.89 (1H, dd, J=2.5, 0.6 Hz), 8.76 (1H, q, J=4.7 Hz), 8.22 (1H, dd, J=8.4, 2.5 Hz), 8.03 (1H, dd, J=8.4, 0.6 Hz), 7.65 (1H, dd, J=14.2, 2.1 Hz), 7.56 (1H, dd, J=8.5, 2.1 Hz), 7.13 (1H, t, J=8.5 Hz), 4.37 (1H, d, J=3.1 Hz), 3.78 (1H, m), 3.71 (1H, m), 3.21-3.38 (3H, m), 3.07 (1H, d, J=11.4 Hz), 2.81 (3H, d, J=4.7 Hz), 2.64-2.74 (2H, m), 2.18-2.26 (1H, m), 1.60-1.91 (8H, m), 1.39-1.51 (3H, m), 1.21-1.30 (2H, m).

Reference： [1]Patent: US2008/318991,2008,A1 .Location in patent: Page/Page column 10

11
[ 945863-21-8 ]
[ 1197340-73-0 ]
C₂₇H₂₆N₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;polyethylene supported palladium catalyst (FibreCat FC 1007); In ethanol; water; at 115℃; for 0.25h;Microwave irradiation;	Step 2 To a solution of 3-(4-bromophenyl)-4-(4-methoxybenzyloxy)-1 -methyl- 1 H- pyrazole-5-carboxylate T-12 (400 mg, 0.96 mmol) in ethanol (10 mL) and water (1 mL) were added 2-(N-methylamidocarboxy)-5-pyridineboronic acid pinacol ester (254 mg, 0.97 mmol), potassium carbonate (138 mg, 1.0 mmol) and polyethylene supported palladium catalyst (FibreCat FC 1007, 3 % Pd, 300 mg). The reaction mixture was heated in a microwave reactor at 115 0C for 15 minutes. To the reaction mixture was added lithium hydroxide monohydrate (127 mg, 3.0 mmol). The reaction mixture was heated in a microwave reactor at 1 15 0C for 20 minutes. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The crude product was purified by RP- HPLC to afford the desired 4-(4-methoxybenzyloxy)-1 -methyl-3-(4-(6-(methylcarbamoyOpyridin-S-yOphenyO-I H-pyrazole-delta-carboxylic acid T-13 (304 mg, 0.64 mmol).

Reference： [1]Patent: WO2009/143039,2009,A2 .Location in patent: Page/Page column 182; 183

12
[ 845305-87-5 ]
[ 73183-34-3 ]
[ 945863-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 110℃; for 1h;Inert atmosphere; Microwave irradiation;	Example 6; Preparation of 5-(2-Acetamidothiazolo[5,4-Z>]pyridin-5-yl)-N- methylpicolinamide (6); PcIdPPfCI2-CH2CI2 KOAc, 1 ,4-dioxane microwave, 110 0C Example 1 ditbpfPdCI2, Cs2CO3 NaHCO3(Sat.), DMF, microwave, 110-120 0C[0381] A mixture of 5-bromo-N-methylpicolinamide (320 mg, 1.48 mmol), bispinacolatodiboron (752 mg, 2.96 mmol), PddppfCl2-DCM (cat.), KOAc (436 mg, 4.44 mmol) in 1,4-dioxane (5 mL, degassed) was heated at 110 0C in a microwave for 1 h. To this mixture was then added Example 1 (608 mg, 2.22 mmol), ditbpfPdC12 (cat.), Cs2CO3 (1.45 g, 4.44 mmol), NaHCO3 (sat., 1 mL) and DMF (dry, degassed, 1 mL). It was heated in a microwave at 1100C for 1 h, then at 120 0C for another hour. The reaction mixture was purified by HPLC to give the titled compound as a white solid. 1H NMR (400 MHz, DMSO-rfbeta) delta ppm 12.53 (s, IH), 9.28 (d, J=4 Hz, IH), 8.79 (m, IH), 8.61 (dd, J=8 Hz, IH), 8.18 (m, 2H), 8.08 (d, J=8 Hz, IH), 2.78 (d, J=4 Hz, IH), 2.18 (s, 3H); [M+H] calc'd for Ci5Hi3N5O2S, 328; found, 328.

Reference： [1]Patent: WO2010/8847,2010,A2 .Location in patent: Page/Page column 125-126

13
[ 945863-21-8 ]
[ 1112982-76-9 ]
[ 1204741-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; caesium carbonate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In 1,4-dioxane; water; N,N-dimethyl-formamide; at 110 - 120℃; for 2h;Inert atmosphere; Microwave irradiation;	Example 6; Preparation of 5-(2-Acetamidothiazolo[5,4-Z>]pyridin-5-yl)-N- methylpicolinamide (6); PcIdPPfCI2-CH2CI2 KOAc, 1 ,4-dioxane microwave, 110 0C Example 1 ditbpfPdCI2, Cs2CO3 NaHCO3(Sat.), DMF, microwave, 110-120 0C[0381] A mixture of 5-bromo-N-methylpicolinamide (320 mg, 1.48 mmol), bispinacolatodiboron (752 mg, 2.96 mmol), PddppfCl2-DCM (cat.), KOAc (436 mg, 4.44 mmol) in 1,4-dioxane (5 mL, degassed) was heated at 110 0C in a microwave for 1 h. To this mixture was then added Example 1 (608 mg, 2.22 mmol), ditbpfPdC12 (cat.), Cs2CO3 (1.45 g, 4.44 mmol), NaHCO3 (sat., 1 mL) and DMF (dry, degassed, 1 mL). It was heated in a microwave at 1100C for 1 h, then at 120 0C for another hour. The reaction mixture was purified by HPLC to give the titled compound as a white solid. 1H NMR (400 MHz, DMSO-rfbeta) delta ppm 12.53 (s, IH), 9.28 (d, J=4 Hz, IH), 8.79 (m, IH), 8.61 (dd, J=8 Hz, IH), 8.18 (m, 2H), 8.08 (d, J=8 Hz, IH), 2.78 (d, J=4 Hz, IH), 2.18 (s, 3H); [M+H] calc'd for Ci5Hi3N5O2S, 328; found, 328.

Reference： [1]Patent: WO2010/8847,2010,A2 .Location in patent: Page/Page column 125-126

14
[ 945863-21-8 ]
[ 1233526-85-6 ]
[ 1233526-81-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 120℃; for 3h;Inert atmosphere;	Step 5: 5-{2-[2-amino-6-(4-methylpipera?in-l-yl)pyrimidm-4-yl]-6-fluoro-l,2JJ-ten-ahydroisoquitwlin- 7-yl}-N-methylpyridine-2-carboxamide; , N .C )NHjN ^ ^ N A mixture of 4-(7-bromo-6-fluoro-3,4-dihydroisoquinolin-2(l H)-yl)-6-(4-methylpiperazin-l- 5 yl)pyrimidin-2-amine (0.025 g, 0.060 mmol), N-methyl-5-(4s4,5,5-tetramethyl-L3,2-dioxaborolan-2- yl)pyridine-2-carboxamide (0.0140 g,Frontier, Cat. No. M 10074) in 1,4-dioxane (0.36 mL) was stirred at r.t. for 10 min. Potassium carbonate (37.8 mg, 0.274 mmo.) in water (0.18 mL) was added. The mixture was degassed and refilled with nitrogen three times [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1: 1) (3.0 mg, 10 0.0036 mmol) was added and the mixture was degassed and refilled with nitrogen three times and then heated at 120 0C )(oil bath temperature) for 3 h. After cooling, the mixture was diluted with methanol, and filtered. The filtrate was purified on RP-HPLC (pH = 10) to afford the desired product. LCMS (M+H)+: m/z = 477.2.

Reference： [1]Patent: WO2010/75270,2010,A1 .Location in patent: Page/Page column 183

15
[ 945863-21-8 ]
[ 1233524-18-9 ]
[ 1233524-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 120℃; for 2h;	Example 25-{2-(2-Amino-6-(4-methylpiperazin-l-yI)pyrimidin-4-yl]-l^y3,4-tetrahydroisoquinolin-7-yl}-N- methyIpyrdine-2-carboxaraide; A mixture of 4-(7-bromo-3,4-dihydroisoquinolin-2(lH)-yl)-6-(4-methylpiperazin-l-yl)pyrimidin- 2-amine (15 mg, 0.037 mmol, Example 1), N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridine-2-carboxamide (15 mg, 0.056 mmol, Frontier, Cat. No. M10074), [1,1'- Bis(diphenylphosphino)ferrocene] dichloropalladium(H), complex with dichloromethane (1: 1 ) (1.8 mg, 0.0022 mmol, Aldrich Cat. No. 379670), 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]Patent: WO2010/75270,2010,A1 .Location in patent: Page/Page column 60

Yield	Reaction Conditions	Operation in experiment
53%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 12h;Inert atmosphere;	General procedure: Intermediate 9: 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Potassium acetate (0.627 g, 6.39 mmol) and bis(pinacolato)diboron (0.595 g, 2.34 mmol) were added to a solution of 4-bromo-2-chlorobenzamide (0.500 g, 2.13 mmol) in dioxane 3.6 ml), and the solution was degassed for 30 min. To this solution [1,1'-bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (0.052 g, 0.063 mmol) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as a brown solid (0.75 g, 69%). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.91 (s, 1H), 7.89 (m, 1H), 7.61 (m, 2H), 7.44 (d, J=7.6 Hz, 1H), 1.14 (s, 12H).
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 12h;Inert atmosphere;	General procedure: Intermediate 9: 2-chloro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide: Potassium acetate (0.627 g, 6.39 mmol) and bis(pinacolato)diboron (0.595 g, 2.34 mmol) were added to a solution of 4-bromo-2-chlorobenzamide (0.500 g, 2.13 mmol) in dioxane 3.6 ml), and the solution was degassed for 30 min. To this solution [Iota, - bis(diphenylphosphino)ferrocene]dichloro palladium(II).CH2Cl2 (0.052 g, 0.063 mmol) was added under nitrogen atmosphere and heated to 80C. After 12h, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as a brown solid (0.75 g, 69%). 'H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.91 (s, 1H), 7.89 (m, 1H), 7.61 (m, 2H), 7.44 (d, J = 7.6 Hz, 1H), 1.14 (s,12H).
500 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 150℃; for 2h;Inert atmosphere; Microwave irradiation;	General procedure: 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.

17
[ 945863-21-8 ]
[ 1200498-30-1 ]
[ 1200498-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 70℃; for 0.5h;microwave;	Seventh step To the compound (124) (47 mg), N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)picolinamide (38 mg) and PdCl2 (dppf) (9.11 mg) was added DME (1 m), a sodium carbonate aqueous solution (1 mol/L: 0.335 mL) was added, microwave was irradiated at 70C, and the mixture was stirred for 30 minutes. The resulting reaction solution was subjected to chromatography to afford the crude product (125) (24 mg).

Reference： [1]Patent: EP2305672,2011,A1 .Location in patent: Page/Page column 86

18
[ 945863-21-8 ]
[ 69249-22-5 ]
[ 1332952-05-2 ]

Yield	Reaction Conditions	Operation in experiment
45.54%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 1.5h;	Step 1: 5-(3-Amino-1,2,4-triazin-6-yl)-N-methylpyridine-2-carboxamide A mixture of N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (200 mg, 0.80 mmol) (VWR, Cat. No. 200068-640), <strong>[69249-22-5]6-bromo-1,2,4-triazin-3-amine</strong> (130 mg, 0.76 mmol, Example 2, Step 1), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.04 mmol) and potassium carbonate (0.32 g, 2.3 mmol) in toluene (1.3 mL), ethanol (0.66 mL) and water (0.66 mL) was heated at 120 C. for 1.5 h. The mixture was filtered and washed with methanol. The filtrate was purified by RP-HPLC (pH=10) to afford the desired product (80 mg, 45.54%). LCMS (M+H)+: m/z=231.4; LCMS (M+H+H2O)+: m/z=249.3.

Reference： [1]Patent: US2011/212967,2011,A1 .Location in patent: Page/Page column 13

19
[ 945863-21-8 ]
[ 1332450-86-8 ]
[ 1332448-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 14h;	Example No. 71: Preparation of Compound No. 71[0359] 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-l,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) delta (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]Patent: WO2012/112962,2012,A1 .Location in patent: Page/Page column 162

20
[ 945863-21-8 ]
[ 1332450-87-9 ]
[ 1332448-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 0.75h;Inert atmosphere;	Example No. 73: Preparation of Compound No. 73[0361] 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, 0.276 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 t ^ i over annyarous sodium sulfate and concentrated under reduced pressure to anora cruae material, which was purified by reverse phase HPLC. 1H NMR (TFA salt, CD3OD) delta (ppm): 8.1-8.27 (m, 1H), 8.0 (s, 1H), 7.8 (m, 2H), 7.42 (m, 1H), 7.3 (s, 1H), 6.9-7.0 (m, 2H), 4.76 (d, 1H), 4.38 (d, 1H), 3.7 (m, 1H), 3.5 (m, 1H), 3.0 (m, 4H), 2.88 (s, 3H), 2.93 (m, 1H), 2.4 (s, 3H).

Reference： [1]Patent: WO2012/112962,2012,A1 .Location in patent: Page/Page column 162-163

21
[ 945863-21-8 ]
[ 1332450-89-1 ]
[ 1332448-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; H'2O (water); at 90℃; for 0.75h;	Example No. 75: Preparation of Compound No. 75[0363] 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 K2CO3 (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) delta (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]Patent: WO2012/112962,2012,A1 .Location in patent: Page/Page column 163

22
[ 945863-21-8 ]
6-bromo-4-(((4R,5R)-2-(2-hydroxy-2-methylpropanoyl)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
4-(((4R,5R)-2-(2-hydroxy-2-methylpropanoyl)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)-6-(6-(methylcarbamoyl)-3-pyridinyl)pyrrolo[1,2-b]pyridazine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium phosphate; In water; N,N-dimethyl-formamide; at 90℃; for 1h;Inert atmosphere;	Step 2: 4-(((3aS,4R,5R,6aS)-2-(2-hydroxy-2-methylpropanoyl)-4- methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)-6-(6-(methylcarbamoyl)-3- pyridinyl)pyrrolo[l,2-b]pyridazine-3-carboxamide (Example 63)[00308] A mixture of 6-bromo-4-(((3aS,4R,5R,6aS)-2-(2-hydroxy-2- methylpropanoyl)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[l,2- b]pyridazine-3-carboxamide (32 mg, 0.055 mmol), N-methyl-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)picolinamide (29.0 mg, 0.11 1 mmol) and 2.0 M aqeous K3PO4 (0.1 1 1 mL, 0.221 mmol) in dimethylformamide (1 mL) was heated to 90 C under nitrogen for 1 h. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles;Guard Column: Waters XBridge C18, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5acetonitrile:water with 10-mM ammonium acetate; Gradient: 0-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give the title compound (14.9 mg, 52% yield). 1H NMR (500MHz, 1 : 1 mixture of d 8.93 (d, J=2.0 Hz, 1H), 8.28 - 8.08 (m, 3H), 8.04 (d, J=1.5 Hz, 1H), 7.28 (d, J=1.5 Hz, 1H), 4.45 - 4.19 (m, 2H), 4.03 - 3.91 (m, 1H), 3.77 - 3.56 (m, 2H), 3.10 - 2.99 (m, 3H), 2.96 - 2.79 (m, 2H), 2.53 - 2.32 (m, 1H), 1.87 - 1.75 (m, 1H), 1.66 - 1.54 (m, 1H), 1.51 - 1.35 (m, 6H), 1.22 (d, J=6.4 Hz, 3H); MS (ES+) m/z: 520.2 (M+H); LC retention time: 1.135 min (analytical HPLC Method I).

Reference： [1]Patent: WO2012/125893,2012,A1 .Location in patent: Page/Page column 171

23
[ 945863-21-8 ]
[ 1610611-85-2 ]
[ 1610611-12-5 ]

Yield	Reaction Conditions	Operation in experiment
13%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere; Sealed tube;	General procedure: A solution mixture of bromo compound (1 .0 equivalent), boronic acid (1.3 equiv) and aq. 1 N Na2CO3 (2.0 equivalent) in 1, 4-dioxane (0.1 M) taken in a sealed tube was degassed with argon for about 20 mi Pd(PPh3)4 (0.1 equivalent) was added under argon atmosphere. The resulting reaction mixture was stirred at 90 - 100 C for 2-16 h. The reaction mixture cooled to room temperature and filtered through celite. The filterate was taken in to water and ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by silica (100-200 mesh) column chromatography using a solvent gradient of 1-2% methanol in chloroform as eluant. Some instances compounds were further purified by prep-TLC or prep-HPLC to obtain as yellow solids. Compound 97 was prepared using the general procedure described in Suzuki Procedure G with the appropriate starting materials. Yield 13%. Yellow solid. 1H-NMR (400 MHz, DMSO-d6): c5 8.82 (d, J = 1.3 Hz, 1 H), 8.69-8.74 (m, 2H), 8.63 (5, 1 H), 8.06-8.10 (m, 2H), 7.96 (5, 1 H), 7.83 (d, J = 8.8 Hz, 2H), 7.55 (d, J = 8.8 Hz, 2H), 6.85 (dd, J = 1.8, 7.5 Hz, 1 H), 3.46 (5, 3H), 2.86 (d, J = 4.9 Hz, 3H). ESl-LC/MS: m/z 411 .20 (M+H); R = 2.41 mm [Waters Acquity UPLC with Quattro micro TQD; Waters Acquity BEH Cl 8, 1.7 pm, 2.1 X 50mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) hold for 0.5 mm to 10:90 H2Q (0.025% TEA) :CH3CN (0.025% TEA) in 2.5 mm and hold for 2 mm with flow rate of 0.4 mL/min]. HPLC purity: 98.3% at 254 nm; R = 3.05 mm [Waters Acquity UPLC with PDA detector; Waters Acquity BEH 018, 1.7 pm, 2.1 X 100 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) to 20:80 H20 (0.025% TEA):CH3CN (0.025% TEA) in 4 mm and hold for 2 mm with flow rate of 0.3 mL/min].

Reference： [1]Patent: WO2014/78802,2014,A1 .Location in patent: Page/Page column 73; 164; 165

24
[ 945863-21-8 ]
[ 1610612-29-7 ]
[ 1610612-38-8 ]

Yield	Reaction Conditions	Operation in experiment
200 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere;	A mixture of tert-butyl 2-(3-bromopyrazolo [1, 5-a] pyridine-5-carbonyl)-2-(4-cyanophenyl)- 1-methylhydrazinecarboxylate (500 mg, 1.06 mmol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (558 mg, 2.13 mmol) and K2003 (323 mg, 2.34 mmol) in dioxane: water (3:1) (10 mL) was degassed with argon for about 10 mm. To the resulting solution were added Pd012(dppf).0H2012 (174 mg, 0.213 mmol) and the reaction mixture was maintained at 90 0 for 16 h. The reaction mixture was filtered through celite and the celite pad was washed with ethyl acetate (50 mL). The filtrate was concentrated and the residue was purified by column chromatography over silica (100-200 mesh) using a solvent gradient of 1% methanol in chloroform as eluant to afford 200 mg (36%) of tertbutyl 2-(4-cyanophenyl)- 1 -methyl-2-(3-(6-(methylcarbamoyl)pyridin-3-yI)pyrazolo[1 , 5- a]pyridine-5-carbonyl)hydrazinecarboxylate 92a as an yellow color solid. 1H NMR (300 MHz, DMSO-d6): 6 8.90 (5, 1 H), 8.84-8.86 (m, 1 H), 8.71-8.73 (m, 1 H), 8.69 (5, 1 H), 8.18 (m, 2H), 8.08-8.11 (m, 1H), 7.92 (d, J= 6.9 Hz, 2H), 7.47-7.56 (m, 2H), 6.94-7.06 (m, 1H), 3.14 (s, 3H), 2.85(d, J=4.8 Hz, 3H), 1.32 (s, 9H); ESI-LC/MS m/z526.03 (M÷H); r.t. =2.81 [Waters Acquity UPLC with QuattroMicro; Waters Acquity BEH 018, 1 7pm,2.lx5Omm column; gradient of 98:2 H20 (0.025% TEA): CH3CN (0.025%TFA) to 0:100H20 (0.025% TFA):CH3CN (0.025%TFA) for 5 minutes with 0.4 mL/min flow rate].

Reference： [1]Patent: WO2014/78802,2014,A1 .Location in patent: Page/Page column 154; 155

25
[ 945863-21-8 ]
[ 1610612-29-7 ]
5-(5-(1-(4-cyanophenyl)-2-methylhydrazinecarbonyl)pyrazolo[1,5-a]pyridin-3-yl)-N-methylpicolinamide [ No CAS ]

Reference： [1]Patent: WO2014/78802,2014,A1

26
[ 945863-21-8 ]
[ 1610612-31-1 ]
[ 1610611-75-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 2h;Inert atmosphere;	To a stirred solution of 3-bromo-N-ethyl-N-(5-fluoropyridin-2-yl)pyrazolo[1 ,5-a]pyridine-5- carboxamide 95-2 (500 mg, 1 .377 mmol) in dioxane: water (3:1) (10.0 mL), N-methyl-5- (4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)picolinam ide (723.3 mg, 2.762 m mol), K2003 (419 mg , 3.036 mmol) were added and degassed with argon for about 15 mm. PdCI2(dppf )CH2CI2 complex (225.3 mg, 0.275 mmol) was added under argon atmosphere. The resulting reaction mixture was maintained at 80 0 for 2 h, cooled to room temperature and filtered through celite. The filtrate was partitioned between water (100 mL) and ethyl acetate (100 mL). The ethyl acetate layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 60-70 % ethyl acetate in pet-ether as eluant to afford 300 mg (52 %) of N-ethyl-N-(5- fluoropyridin-2-yI)-3-(6-(methylcarbamoyl)pyridin-3-yI)pyrazolo[1 , 5-a]pyridine-5- carboxamide 159 as a pale-yellow color solid. 1HNMR (400 MHz, DMSO-d6): c5 8.82 (5, 1 H), 8.67-8.74 (m, 2H), 8.62 (5, 1 H), 8.46 (d, J = 3.0 Hz, 1 H), 8.09 (5, 2H), 7.87 (5, 1 H), 7.73(td, J=3.3, 8.4 Hz, 1H), 7.42 (dd, J=3.6, 8.8 Hz, 1H), 6.77 (dd, J= 1.8, 7.3 Hz, 1H),4.01 (q, J= 7.0 Hz, 2H), 2.86 (d, J= 4.8 Hz, 3H), 1.17 (t, J= 7.0 Hz, 3H). ESI-LC/MS: m/z417.3 (M-H); R = 3.23 mm [Agilent [C with Ion trap Detector; XBridge-C18, 3.5 pm, 4.6 X75 mm column; gradient of 80:20 H20 (0.005 M ammonium bicarbonate): CH3CN to 20:80 H20 (0.01 M ammonium bicarbonate):CH3CN in 4.0 mm and hold for 3.0 mm with flow rate of 1.0 mLJmin]. HPLC purity: 98.1% at 254 nm; R = 1.92 mm [Waters Acquity UPLC with PDA; Waters Acquity UPLC BEH 018, 1 .7 pm, 2.1 X 100 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) to 10:90 H20 (0.025% TEA) :CH3CN (0.025% TEA) in 4.0 mm and hold for 2.0 mm with flow rate of 0.3 mLJmin].

Reference： [1]Patent: WO2014/78802,2014,A1 .Location in patent: Page/Page column 245; 246

27
[ 945863-21-8 ]
[ 1610612-41-3 ]
[ 1610611-24-9 ]

Yield	Reaction Conditions	Operation in experiment
15%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; Sealed tube;	General procedure: A solution mixture of bromo compound (1 .0 equivalent), boronic acid (1.3 equiv) and aq. 1 N Na2CO3 (2.0 equivalent) in 1, 4-dioxane (0.1 M) taken in a sealed tube was degassed with argon for about 20 mi Pd(PPh3)4 (0.1 equivalent) was added under argon atmosphere. The resulting reaction mixture was stirred at 90 - 100 C for 2-16 h. The reaction mixture cooled to room temperature and filtered through celite. The filterate was taken in to water and ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by silica (100-200 mesh) column chromatography using a solvent gradient of 1-2% methanol in chloroform as eluant. Some instances compounds were further purified by prep-TLC or prep-HPLC to obtain as yellow solids. Compound 97 was prepared using the general procedure described in Suzuki Procedure G with the appropriate starting materials. Yield 13%. Yellow solid. 1H-NMR (400 MHz, DMSO-d6): c5 8.82 (d, J = 1.3 Hz, 1 H), 8.69-8.74 (m, 2H), 8.63 (5, 1 H), 8.06-8.10 (m, 2H), 7.96 (5, 1 H), 7.83 (d, J = 8.8 Hz, 2H), 7.55 (d, J = 8.8 Hz, 2H), 6.85 (dd, J = 1.8, 7.5 Hz, 1 H), 3.46 (5, 3H), 2.86 (d, J = 4.9 Hz, 3H). ESl-LC/MS: m/z 411 .20 (M+H); R = 2.41 mm [Waters Acquity UPLC with Quattro micro TQD; Waters Acquity BEH Cl 8, 1.7 pm, 2.1 X 50mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) hold for 0.5 mm to 10:90 H2Q (0.025% TEA) :CH3CN (0.025% TEA) in 2.5 mm and hold for 2 mm with flow rate of 0.4 mL/min]. HPLC purity: 98.3% at 254 nm; R = 3.05 mm [Waters Acquity UPLC with PDA detector; Waters Acquity BEH 018, 1.7 pm, 2.1 X 100 mm column; gradient of 90:10 H20 (0.025% TEA): CH3CN (0.025% TEA) to 20:80 H20 (0.025% TEA):CH3CN (0.025% TEA) in 4 mm and hold for 2 mm with flow rate of 0.3 mL/min].

Reference： [1]Patent: WO2014/78802,2014,A1 .Location in patent: Page/Page column 73; 164; 165; 177

28
[ 945863-21-8 ]
[ 1610612-51-5 ]
[ 1610611-59-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere;	A solution mixture of 3-bromo-N-(4-cyanophenyl)-N-cyclobutylpyrazolo[1 ,5-a]pyridine-5- carboxamide 112-2 (3.0 g, 7.57 mmol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (3.99 g, 15.229 mmol), K2003 (2.3 g, 16.66 mmol) in dioxane: water (3:1) (60.0 mL) were degassed with argon for about 15 mm. PdCI2(dppf).CH2CI2 complex (1 .24 g, 1 .518 mmol) was added to the reaction mixture under argon atmosphere. The reaction mixture was maintained at 100 0 for 2 h, cooled to room temperature and filtered through celite. The filtrate was partitioned between water (100 mL) and ethyl acetate (100 mL). The ethyl acetate layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 70 % ethyl acetate in pet-ether as eluant to afford 1 .8 g (53 %) of N-(5-cyanopyridin-2-yl)-N- cyclobutyl-3-(6-(methylcarbamoyl)pyridin-3-yl)pyrazolo[1 ,5-a]pyridine-5-carboxam ide 144 as a Light yellow color solid. 1H-NMR (300 MHz, DMSO-d6): c5 8.96 (d, J= 2.4 Hz, 1 H), 8.81 (5, 1 H), 8.67-8.74 (m, 2H), 8.62 (5, 1 H), 8.33 (dd, J= 2.4 Hz, 8.1 Hz, 1 H), 8.05-8.14 (m, 2H), 7.84 (5, 1H), 7.62 (d, J= 8.4 Hz, 1H), 6.79 (dd, J= 1.5, 7.2 Hz, 1H), 4.90-4.95 (m, 1 H), 2.86 (d, J= 4.8 Hz, 3H), 2.19-2.27 (m, 2H), 2.07-2.13 (m, 2H), 1.58- 1.69 (m, 2H). ESI-LC/MS: m/z452.39 (M+H); R = 2.25 mm [Waters Acquity UPLC with SOD; Waters Acquity UPLC BEH 018, 1.7 pm, 2.1 X 50 mm column; gradient of 95:05 H20 (0.1% H000H): CH3CN (0.1% H000H) hold for 0.5 mm and to 50:50 H20 (0.1% H000H):CH3CN (0.1% H000H) in 1.7 mm and to 0:100 H20 (0.1% H000H):CH3CN (0.1% H000H) in 3.0 mm and hold for 2.0 mm with flow rate of 1.0 mL/min]. HPLC purity:98.5% at 254 nm; R = 2.05mm [Waters Acquity UPLC with PDA; Waters Acquity UPLC BEH 018, 1 .7 pm, 2.1 X 50 mm column; gradient of 98:02 H20 (0.025% TEA): CH3CN (0.025% TEA) to 10:90 H20 (0.025% TEA):CH3CN (0.025% TEA) in 2.5 mm and hold for 3.5 mm with flow rate of 0.3 mL/min].

Reference： [1]Patent: WO2014/78802,2014,A1 .Location in patent: Page/Page column 227; 228

29
[ 945863-21-8 ]
[ 1618663-35-6 ]
[ 1618663-63-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 85℃; for 2h;Sealed tube; Inert atmosphere;	2-Chloro-5-iodo-4-(tetrahydro-2H-pyran-4-yloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (1 equiv), 1?-bis(diphenyl-phosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (0.1 equiv), sodium carbonate (3 equiv) were suspended in a 3:1 mixture of 1,4-dioxane and water (0.09 M) were combined in a sealed reaction vessel. The resulting solution was flushed with nitrogen and stirred at 85 C. for 2 h. After cooling to room temperature the reaction mixture was loaded directly onto a silica-gel column and purified using flash chromatography (0-55% ethyl acetate in hexane). Fractions were combined, concentrated and the residue dried under high vacuum to give the title compound (61% yield) as a brown semi solid. MS (ESI) m/z 519.1 [M+1]+.

Reference： [1]Patent: US2014/200206,2014,A1 .Location in patent: Paragraph 0324

30
[ 945863-21-8 ]
[ 1533424-29-1 ]
5-[4-(5-amino-1H-[1,2,4]triazol-3-ylamino)-2-chloro-6-trifluoromethylphenyl]pyridine-2-carboxylic acid methylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 105℃; for 18h;Sealed tube; Microwave irradiation; Inert atmosphere;	A mixture of N3-(4-bromo-3-chloro-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 1 (200 mg, 561 flmol, Eq: 1.00), N-methyl-5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)picolinamide [945863-21-8] (198 mg, 757 flmol, Eq: 1.35) and (triphenylphosphine)palladium (0) (64.8 mg, 56.1 flmol, Eq: 0.1) was degassed (vacuum I nitrogen cycles) then degassed dry dioxane (1.85 ml) (nitrogen bubbling with sonication) and a degassed (nitrogen bubbling with sonication) 2M solution of sodium carbonate in water (561 f..Ll,1.12 mmol, Eq: 2) were added. The reaction mixture was sealed and stirred at 105 oc for18h.The reaction mixture was adsorbed unto silica (1g), concentrated and purified on silica gel (silica 24g, dichloromethane/methanol 97:3 to 70:30). One fraction was isolated and dried in vacuo to afford 45 mg (20%) of the desired product as a yellow semi-solid solid.MS +mlz: 411.9 (M+H)+

Reference： [1]Patent: WO2014/135471,2014,A1 .Location in patent: Page/Page column 108; 109

31
[ 945863-21-8 ]
rac-(6S,7R,8R)-5-acetyl-6-cyclopropyl-7-methyl-8-(phenylamino)-5,6,7,8-tetrahydro-1,5-naphthyridin-2-yl trifluoromethanesulfonate [ No CAS ]
rac-5-((6S,7R,8R)-5-acetyl-6-cyclopropyl-7-methyl-8-(phenylamino)-5,6,7,8-tetrahydro-1,5-naphthyridin-2-yl)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 4h;Inert atmosphere;	A mixture of rac-(6S,7R,8R)-5-acetyl-6-cyclopropyl-7-methyl-8-(phenylamino)-5,6,7,8-tetrahyd ro- 1,5-naphthyridin-2-yl trifluoromethanesulfonate (for a preparation see Intermediate 102, 75 mg, 0.160mmol), potassium carbonate (66.2 mg, 0.479 mmol), PdCI2(dppf) (17.53 mg, 0.024 mmol) and Nmethyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinamide (50.2 mg, 0.192 mmol) in 1,4- dioxane (1.400 mL) and water (0.35 mL) was stirred under nitrogen at 100C for 4 h. The reaction mixture was concentrated in vacuo then dissolved in DCM. This solution was washed with water(3x10 mL), dried through a hydrophobic frit and concentrated in vacuo to give a dark red gum. The samples were dissolved in 1:1 MeOH:DMSO (2x1 mL) and purified by MDAP (HpH). The solvent was evaporated in vacuo. The sample was dissolved in MeOH (2 mL) and was applied to a 2 g Flash SCX SPE column which had been pre-equilibriated with MeOH (10 mL). The column was flushed with MeOH (10 mL) then with MeOH/NH3 (2 M, 10 mL). The MeOH/NH3 fraction wascollected and the solvent was evaporated to give the product (14 mg, 0.031 mmol, 19%) as a yellow gum. LCMS (2 mm Formic): Rt = 1 .09 mi [MH] = 456.

Reference： [1]Patent: WO2014/140076,2014,A1 .Location in patent: Page/Page column 290

32
[ 945863-21-8 ]
C₂₅H₂₉BrN₂O₅ [ No CAS ]
C₃₂H₃₆N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Inert atmosphere; Irradiation;	116A. Ethyl 2-(4-(5-(6-(methylcarbamoyl)pyridin-3-yl)-l,2,3,4- tetrahydroisoquinoline-l-carboxamido)phenyl)acetate, 2 TFA: POCI3 (0.052 mL, 0.561 mmol) was added dropwise to a mixture of Intermediate 6 (0.200 g, 0.561 mmol) and ethyl 2-(4-aminophenyl)acetate (0.111 g, 0.618 mmol) in pyridine (2.0 mL) at -15 C for 30 minutes and then gradually allowed to come to room temperature. The, reaction was quenched with water, extracted with EtOAc, washed with l.ON HCl solution (3x), water, saturated aHC03 solution, brine, dried over sodium sulfate, filtered, and concentrated. This material, N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)picolinamide (0.221 g, 0.842 mmol), and Cs2C03 (0.549 g, 1.684 mmol) were added to DME/H20 (5: 1; 12 mL) and degassed for 15 minutes. Tetrakis-(triphenylphosphine)palladium(0) (0.065 g, 0.056 mmol) was added and the complete mixture irradiated at 120 C for 15 minutes. The reaction mixture was poured into EtOAc, washed with saturated NaHC( solution, brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by normal phase column chromatography The boc group was removed by treatment with 50% TFA/DCM for 2 h, concentrating, purifying by reverse phase prep HPLC, and concentrating to give 116A (0.090 g, 0.128 mmol, 23% yield) as a tan solid. MS (ESI) m/z: 473 (M+H)+.

Reference： [1]Patent: WO2014/160668,2014,A1 .Location in patent: Page/Page column 226-227

33
[ 945863-21-8 ]
ethyl 6-bromo-2-[(tert-butoxycarbonyl)amino]furo[3,2-b]pyridine-3-carboxylate [ No CAS ]
ethyl 2-[(tert-butoxycarbonyl)amino]-6-{6-[(methylamino)carbonyl]pyridin-3-yl}furo[3,2-b]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 85℃; for 1.5h;Inert atmosphere;	Step A. ethyl 2-[(tert-butoxycarbonyl)amino]-6-{6-[(methylamino)carbonyl]pyridin-3-yl}furo[3,2-b]pyridine-3-carboxylate A mixture of ethyl 6-bromo-2-[(tert-butoxycarbonyl)amino]furo[3,2-b]pyridine-3-carboxylate (0.300 g, 0.779 mmol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine-2-carboxamide</strong> (0.2654 g, 1.012 mmol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide</strong>, DIPEA (0.27 mL, 1.6 mmol) in 1,4-dioxane (4 mL) and water (0.2 mL) was deoxygenated and purged with N2 several times prior to the addition of Pd(tBu3P)2 (0.0796 g, 0.16 mmol). The reaction mixture was heated at 85 C. for 1.5 h. Upon cooling to ambient temperature the reaction mixture was diluted with EtOAc and was filtered through a pad of diatomaceous earth. The resulting filtrate was washed with water, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel flash column chromatography using a CombiFlash apparatus eluting with EtOAc/hexanes (0-100%) to afford 285 mg of the sub-title compound (83% yield). LCMS calc. for C22H25N4O6 (M+H)+: m/z=441.2. found: 441.2.

Reference： [1]Patent: US2015/57265,2015,A1 .Location in patent: Paragraph 1463; 1464

34
[ 1244041-71-1 ]
[ 945863-21-8 ]
C₁₄H₁₂N₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3189 - 3193

35
[ 1244041-71-1 ]
[ 945863-21-8 ]
C₁₉H₂₀N₄O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3189 - 3193

36
[ 945863-21-8 ]
trifluoro-methanesulfonic acid 2-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-1-methyl-vinylester [ No CAS ]
[ 1572005-19-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; for 0.75h;Reflux;	Example 104 Preparation of Compound No. 122 (1320) To a degassed 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, 0.257 mmol) and potassium carbonate (110 mg, 0.796 mmol), in DME (2 mL) and water (1 mL) were added Pd(PPh3)4 (20 mg, 0.017 mmol) and <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (135 mg, 0.514 mmol) 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) delta (ppm): 8.9 (s, 1H), 8.1-8.21 (m, 2H), 7.3 (s, 1H), 7.19 (s, 1H), 7.1 (m, 2H), 4.76 (d, 1H), 4.4 (d, 1H), 3.82 (bs, 1H), 3.6 (bs, 1H), 3.2 (m, 2H), 3.17 (s, 3H), 3.0 (s, 3H), 2.42 (s, 3H), 2.0 (s, 3H).

Reference： [1]Patent: US2015/266884,2015,A1 .Location in patent: Paragraph 1320

37
[ 945863-21-8 ]
(R)-6-(6-bromo-7-(difluoromethyl)-3,4-dihydroquinolin-1(2H)-yl)-4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one [ No CAS ]
(R)-5-(7-(difluoromethyl)-1-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-6-yl)-1,2,3,4-tetrahydroquinolin-6-yl)-N-methylpicolinamide [ No CAS ]

Reference： [1]Patent: WO2016/55028,2016,A1 .Location in patent: Page/Page column 277

38
[ 945863-21-8 ]
(S)-1-(3-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-1-(tetrahydrofuran-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-c] pyridin-5(4H)-yl)ethanone [ No CAS ]
5-[1-[5-acetyl-1-[(3S)-tetrahydrofuran-3-yl]-6,7-dihydro-4H-pyrazolo [4,3-c]pyridin-3-yl]-3,4-dihydro-2H-quinolin-6-yl]-N-methyl-pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	To a solution of N-methyl-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridine-2- carboxamide (141 mg, 0.54 mmol) and 1-[3-(6-bromo-3,4-dihydro-2H-quinolin-l-yl)-1- [(35)-tetrahydrofuran-3-y[]-6,7-dihydro-4H-pyrazolo [4,3 -c]pyridin-5-yl]cthanone (200 mg, 0.45 mmol) in 1,4-dioxane (2 mL) and water (0.5 mL) was added [1,1?- bis(diphenylphosphino)ferroecnejdichloropalladium(Il), complex with dichloromethane (33mg, 0.04 mmol). The mixture was heated to 100 C for 12 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was filtered and filtrate was concentrated in vacuo. The crude residue was purified by reverse phase chromatography (aeetonitrile 22-16% / 0.2% formic acid in water) to give the title compound (27 mg, 12%) as a yellow solid. ?H NMR (400 MHz, DMSO-d6) oe 8.83 (s, IH), 8.71 - 8.69 (m, IFI), 8.14 (d, J= 8.0 Hz, 114), 8.01 (d,J= 8.8 Hz, 1H), 7.50 (s, 1H), 7.42-7.38 (m, IH), 6.57-6.51 (m,1H), 4.95 - 4.92 (m, IH), 4.14 - 4.12 (m, 2H), 4.02 - 3.90 (m, 2H), 3.83 - 3.80 (m, 4H), 3.60 -3.59 (m, 2H), 2.90 - 2.82 (m, 411), 2.88 (s, 3H), 2.35 - 2.15 (m, 2H), 2.07 - 1.96 (m, 514).LCMS M/Z (M+H) 501.

Reference： [1]Patent: WO2016/86200,2016,A1 .Location in patent: Page/Page column 189

39
[ 945863-21-8 ]
1-(3-(6-bromo-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 ]
5-[1-(5-acetyl-1-tetrahydropyran-4-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-3,4-dihydro-2H-quinolin-6-yl]-N-methyl-pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 110℃; for 12h;Inert atmosphere;	To a solution of 1 -(3 -(6-bromo-3 ,4-dihydroquinolin- l(2F[)-yl)-1 -(tetrahydro-2H-pyran-4-yl)- 6,7-dihydro- I H-pyrazolo[4,3-c]pyridin-5(4H)-yl)ethanone (200 mg, 0.36 mniol) in dioxane (10 mL) and water (2 mL) was added N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)picolinamide (96 mg, 0.36 rnmol), K2C03 (152 mg, 1.10 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (26 mg, 0.03 6 mrnol). The mixture was heated to 110 C for 12 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was concentrated in vacuo. The residue was purified by Prep-TEC (DCM / MeOH = 15: 1) to give the title compound (59 mg, 26%) as a white solid. ?H NMR (400 MHz, CDC13) 8 8.71 (s, JH), 8.20 - 8.17 (m, IH),8.00-7.94 (m, 2H), 7.33 (s, 111), 7.24-7.21 (m, 1H), 6.60 (d,J= 8.0 Hz, 11-I), 4.31 -4.125H), 3.92 (t, J= 6.0 Hz, IH), 3.76 - 3.70 (m, 3H), 3.53 (t, J 12 Hz, 1H), 3.06 (t, J= 4.8 Hz,1.85 (m, 2H). LCMS M/Z (M+H) 515.

Reference： [1]Patent: WO2016/86200,2016,A1 .Location in patent: Page/Page column 197; 198

40
[ 945863-21-8 ]
1-(5-acetyl-1-(tetrahydro-2H-pyran-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-1,2,3,4-tetrahydro-1,7-naphthyridin-6-yl trifluoromethanesulfonate [ No CAS ]
5-[1-(5-acetyl-1-tetrahydropyran-4-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-3,4-dihydro-2H-1,7-naphthyridin-6-yl]-N-methyl-pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	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 0.5h;Microwave irradiation;	To a solution of 1 -(5-acetyl- 1 -(tetrahydro-2H-pyran-4-yl)-4,,5 ,6,7-tetrahydro- iNpyrazolo{4,3 -c]pyridin-3-yl)- 1,2,3 ,4-tetrahydro- 1 ,7-naphthyridin-6-yltrifluoromethanesulfonate (100 mg, 0.19 mmol), N-methyl-5-(4,4,5,5-tetramethyl-. 1,3,2-mmol) in THF (5 mL) and water (1 mL) was added chloro(2-dicyclohexylphosphino-2?,4?,6?-tri-i-propyl- 1,1 ?-biphenyl)(2?-amino- 1,1 ?-biphenyl-2-yl) palladium(lI) (16 mg, 0.02 mmol) and 2-(dicyclohexylphosphino)-2?,4?,6?-triisopropylbiphenyl (8 mg, 0.02 mmol). The mixturewas irradiated in a microwave at 60 C for 0.5 h. After cooling the reaction to room temperature, DCM (50 mL) was added and washed with water (40 mL x 2), The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by Prep-TLC (DCM / MeOH 20/1) to give the title compound (40 mg, 38%) as a yellow solid. ?H NMR (400MHz, DMSO-d6) 9.17 (s, In), 8.79 - 8.72 (m, 1H), 8.47 - 8.45(m, IR), 8.04 (d, J= 8.4 Hz, IH), 7.96 - 7.87 (m, 11-1), 7.83 (s, IH), 4.35 - 4.29 (m, 1H), 4.26- 4.18 (m, 2H), 4.00 - 3.92 (m, 2H), 3.81 - 3.71 (m, 2H), 3.66 - 3.58 (m, 2H), 3.50 - 3.44 (m,2H), 2.93 -2.86 (m, 3H), 2.83 (d,J= 4.8 Hz, 3H), 2.78 -2.71 (m, 111), 2.11 - 1.94 (m, 7H),1.86 - 1.83 (m, 2H). LCMS MZ (M+H) 516.

Reference： [1]Patent: WO2016/86200,2016,A1 .Location in patent: Page/Page column 429; 430

41
[ 945863-21-8 ]
1-(3-(6-bromo-7-chloro-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 ]
5-[1-(5-acetyl-1-tetrahydropyran-4-yl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-3-yl)-7-chloro-3,4-dihydro-2H-quinolin-6-yl]-N-methyl-pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31 mg	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;	To a solution of 1 -(3 -(6-bromo-7-chloro-3,4-dihydroquinolin- 1 (211)-yl)- 1 -(tetrahydro-2H-pyran-4-yI)-6,7-dihydro- 1 H-pyrazolo [4,3 -c]pyridin-5(4I-yl)ethanone (100 mg, 0.2 mmol)in THF (5 mL) and water (1 mL) was added chloro(2-dicyclohexylphosphino-2?,4?,6?-tri-i-propy1-1,P-bipheny1)(2-amino-1,1?-biphenyl-2-yl) palladium(II) (16 mg, 0.02 mmol), 2-(dicyclohexylphosphino)-21,4?,6?-triisopropylbiphenyl (10 mg, 0.02 mmol), N-methyl-5-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)picolinamide (81 mg, 0.3 mmol) and Na2CO3(65 mg, 0.6 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 filtered and concentrated invacuo. DCM (50 mL) was added and the mixture was washed with water (30 mL x 3) andbrine (30 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated 75% / 0.05% NH4OI-1 in water) to give the title compound (31 mg, 27%) as a yellow solid. 111 NMR (400 MHz, DMSO-d6) 8.81 - 8.79 (m, IH), 8.67 - 8.62 (m, 111), 8.08 - 7.97 (m, 2H), 7.19 (s, 11-1), 6.64 - 6.55 (m, 1H), 4.36 - 4.27 (ni, 111), 4.26 - 4.19 (m, 211), 3.98 - 3.95 (m,211), 3.81 -3.70 (m, 211), 3.63-3.55 (m, 2H), 3.49-3.43 (m, 2H), 2.91 -2.76 (m, 711), 2.11 -1.92 (m, 711), 1.86 - 1.83 (m, 211). LCMS MJZ (M+H) 549.

Reference： [1]Patent: WO2016/86200,2016,A1 .Location in patent: Page/Page column 484; 485

42
[ 945863-21-8 ]
4-(1-(6-chloro-2-(pyridin-4-yl)pyrimidin-4-yl)piperidin-4-yl)morpholine [ No CAS ]
N-methyl-5-(6-(4-morpholinopiperidin-1-yl)-2-(pyridin-4-yl)pyrimidin-4-yl)picolinamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6101 - 6120

43
[ 945863-21-8 ]
2-chloro-9H-dipyrido[2,3-b;3’,4’-d]pyrrole [ No CAS ]
N-methyl-5-(9H-pyrrolo[2,3-b:4,5-c']dipyridin-2-yl)pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In 1,4-dioxane; water; at 110℃; for 12h;Inert atmosphere;	General procedure: Procedure D : Suzuki coupling To a solution of 2-chloro-9/-/-pyrrolodipyridine (1 eq) in dioxane:water (6 mL/mmol), the corresponding boronic acid or pinacol ester (1.3 eq), K3P04 (3.0 eq) and X-phos (0.3 eq) were added and the reaction mixture was degassed with argon for 20 min. Pd2(dba)3 (0.1 eq) was added and the reaction mixture was heated at 1 10C for 12 h. The reaction mixture was filtered through a celite pad and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography using 4% methanolic ammonia in DCM to afford the Suzuki coupling product.

Reference： [1]Patent: WO2016/124508,2016,A1 .Location in patent: Page/Page column 31; 36; 37

44
[ 945863-21-8 ]
2-chloro-N,N-dimethyl-9H-pyrrolo[2,3-b:4,5-c']dipyridin-7-amine [ No CAS ]
5-(7-(dimethylamino)-9H-pyrrolo[2,3-b:4,5-c']dipyridin-2-yl)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere;	Example 43. 5-(7-(dimethylamino)-9/-/-pyrrolo[2, 3-fc>:4, 5-c]dipyridin-2-yl)-/V-methylpicolinamide: To a stirred suspension of 2-chloro-/V,/V-dimethyl-9/-/-pyrrolo[2,3-t):4,5-c]dipyridin-7-amine (i54) (0.06 g, 0.24 mmol), /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)picolinamide (0.082 g, 0.312 mmol) in dioxane: water 5:2 (7 ml_), K3P04 (0.155 g, 0.73 mmol) was added and purged with argon for 15 min. Pd2(dba)3 (0.022 g, 0.024 mmol) was then added and the reaction was heated at 100C for 3h. The progress of the reaction was monitored by TLC. After completion , the solvent was evaporated to dryness. The crude product was purified by column chromatography on silica gel (230-400 mesh) using 5% methanol in dichloromethane to afford 5-(7-(dimethylamino)-9H-pyrrolo[2,3-b:4,5-c]dipyridin-2-yl)-/V-methylpicolinamide (0.035g, 42%). 1H NMR (400 MHz, DMSO-d6) delta 2.86 (d, J = 4.8 Hz, 3H), 3.12 (s, 6H), 6.43 (s, 1 H), 7.93 (d, J = 8.0 Hz, 1 H), 8.14 (d, J = 8.2, 1 H), 8.43 (d, J = 8.0 Hz, 1 H), 8.65 (dd, J = 8.2, 2.2 Hz, 1 H), 8.81 (m, 1 H), 8.92 (s, 1 H), 9.34 (s, 1 H), 1 1 .82 (s, 1 H). MS (ESI) m/e (M+1 )+: 347.30

Reference： [1]Patent: WO2016/124508,2016,A1 .Location in patent: Page/Page column 68

45
[ 945863-21-8 ]
4-(2-amino-5-bromo-4-ethylpyridin-3-yl)phenol [ No CAS ]
5-[6-amino-4-ethyl-5-(4-hydroxyphenyl)-3-pyridyl]-N-methylpyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16h;Inert atmosphere;	General procedure: into a 250-ml three-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed 4-(2-amino-5-bromo-4-ethylpyridin-3-yl)phenol (1.0 g, 3.41 mmol), 6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (880 mg, 3.41 mmol,), potassium carbonate (3.3 g, 23.88 mmol), water (30 ml), 1,4-dioxane (25 ml), and Pd(dppf)Cl2 (200 mg, 0.3 mmol). The resulting solution was stirred at 80 C for 16 h, and diluted with 500 ml H2O and 500 ml ethylacetate.The organic layer was washed twice with brine (2 × 250 ml) and concentrated under vacuum. The residue was purified on a silica gel column eluting with DCM/CH3OH (20:1-10:1) to afford the title compound.

Reference： [1]Nature,2017,vol. 550,p. 534 - 538
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 10056 - 10070

46
[ 945863-21-8 ]
5-(8-(5-acetyl-1-(tetrahydro-2H-pyran-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)isoquinolin-3-yl)-N-methylpicolinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 15 - 23

47
[ 945863-21-8 ]
N-methyl-5-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-3-yl)picolinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 15 - 23

48
[ 945863-21-8 ]
3-bromo-8-chloroisoquinoline [ No CAS ]
5-(8-chloroisoquinolin-3-yl)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere;	To a solution of 3-bromo-8-chloro-isoquinoline (0.6 g, 2.5 mmol) in 1,4-dioxane (10 mL) and water (2 mL) was added [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (90 mg, 0.12 mmol), Na2CO3 (0.79 g, 7.42 mmol) and <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (0.68 g, 2.6 mmol). The mixture was heated to 90 oC for 16 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was concentrated in vacuo. EtOAc (50 mL) was added and the mixture was washed with water (30 mL x 2) and brine (30 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (DCM / MeOH = 25 : 1) to give the title compound (0.6 g, 81%) as a yellow solid. LCMS M/Z (M+H) 298.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 15 - 23

49
[ 945863-21-8 ]
8-chloro-4-fluoroisoquinolin-3-yl trifluoromethanesulfonate [ No CAS ]
5-(8-chloro-4-fluoroisoquinolin-3-yl)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 70℃; for 0.5h;Microwave irradiation;	To a solution of 8-chloro-4-fluoroisoquinolin-3-yl trifluoromethanesulfonate (500 mg,1.52 mmol) in 1,4-dioxane (4 mL) and water (1 mL) was added [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (111 mg, 0.15 mmol), Na2CO3 (482 mg, 4.55 mmol) and N-methyl-5-(4,4,5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)picolinamide (398 mg, 1.52 mmol). The mixture was irradiated in a microwave at 70 C for 0.5 h. After cooling the reaction to room temperature, the mixture was filtered and concentrated in vacuo. The cruderesidue was purified by silica gel chromatography (petroleum ether / EtOAc = 3 : 1) to give the title compound (300 mg, 63%) as a yellow solid. LCMS MIZ (M+H) 316.

Reference： [1]Patent: WO2017/205538,2017,A1 .Location in patent: Page/Page column 133; 134

50
[ 945863-21-8 ]
tert-butyl 3,5-difluoro-4-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzyl(methyl)carbamate [ No CAS ]
5-(5-(2,6-difluoro-4-((methylamino)methyl)phenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of Intermediate I (20 mg, 0.032 mmol) in dioxane (1 mL) and water (0.250 mL) was added potassium phosphate, tribasic (13 mg, 0.063 mmol) and <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (16 mg, 0.063 mmol). The mixture was degassed and chloro(2-dicyclohexylphosphino-2?,4?,6?-tri-i-propyl-1,1?-biphenyl)(2?-amino-1,1?-biphenyl-2-yl) palladium(II) (4.98 mg, 6.33 mumol) was added. The resulting mixture was stirred at 90 C. for 2 hours. The mixture was filtered, and 4.0 M HCl solution in dioxane (1 mL, 4.000 mmol) and 1 mL of water were added and the reaction mixture was stirred for another 1 hour at 80 C. 1 mL of methanol was added and the reaction mixture was stirred for another 30 mins at 80 C. The mixture was then diluted with acetonitrile, filtered and purified by prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LC-MS calculated for C20H18F2N7O (M+H)+: m/z=410.2; found 410.2.

Reference： [1]Patent: US2018/72741,2018,A1 .Location in patent: Paragraph 0626-0627

51
[ 945863-21-8 ]
8-(3-cyclopropyl-7-(methylcarbamoyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-1-yl)isoquinolin-3-yl trifluoromethanesulfonate [ No CAS ]
3-cyclopropyl-N-methyl-1-(3-(6-(methylcarbamoyl)pyridin-3-yl)isoquinolin-8-yl)-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;	A suspension of the product from the previous step (300 mg, 0.61 mmol), <strong>[945863-21-8]N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide</strong> (192 mg, 0.73 mmol), PdCl2(dppf) (45 mg, 0.061 mmol), and K2CO3 (253 mg, 1.83 mmol) in 1,4-dioxane (10 mL) and H2O (2 mL) was stirred at 100 C. for 3 h. The mixture was poured into water (50 mL) and extracted with EtOAc (80 mL*3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC (Mobile phase: A=0.1% NH4HCO3/H2O, B=MeCN; Gradient: B=0% to 45% in 18 min; Column: C18) to give the title compound as a yellow solid (35 mg, 12%). MS (ES+): C27H27N7O2 requires: 481, found: 482 [M+H]+. 1H NMR (DMSO-d6) delta 10.04 (s, 1H), 9.46 (appar br s, 1H), 8.88 (q, J=4.9 Hz, 1H), 8.77 (dd, J=8.2, 2.2 Hz, 1H), 8.66 (s, 1H), 8.17 (d, J=8.2 Hz, 1H), 7.98 (d, J=8.2 Hz, 1H), 7.85 (appar t, J=7.6 Hz, 1H), 7.54 (d, J=6.6 Hz, 1H), 6.75 (q, J=4.4 Hz, 1H), 4.69 (s, 2H), 4.14 (t, J=5.4 Hz, 2H), 3.85 (t, J=5.3 Hz, 2H), 2.86 (d, J=4.8 Hz, 3H), 2.56 (d, J=4.3 Hz, 3H), 2.09-2.05 (m, 1H), 1.00-0.93 (m, 4H).

Reference： [1]Patent: US2019/298729,2019,A1 .Location in patent: Paragraph 0599-0601

52
[ 945863-21-8 ]
2-(3-(5-amino-6-chloropyrazin-2-yl)-4-methylphenyl)-3,3,3-trifluoro-2-hydroxypropanamide [ No CAS ]
[ 76-05-1 ]
5-(3-amino-6-(5-(3-amino-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-2-methylphenyl)pyrazin-2-yl)-N-methylpicolinamide bistrifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.4%		General procedure: (1407) A solution of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.026 g, 0.125 mmol) and 2-(3-(5-amino-6-chloropyrazin-2-yl)-4-methylphenyl)-3,3,3-trifluoro-2-hydroxypropanamide (0.015 g, 0.042 mmol) (single enantiomer from step 6) in dioxane (0.832 mL) was treated with sodium carbonate (1.0 M in water) (0.166 mL, 0.166 mmol) and degassed with nitrogen for 5 min. The reaction mixture was treated with dichloro[1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (5.09 mg, 6.24 mumol), degassed with nitrogen for 5 min, and stirred at 120 C. for 2.5 h. The reaction mixture was diluted with THF and filtered through a 0.45 micron cartridge. The cartridge was rinsed with THF and ethyl acetate. The filtrate was concentrated and the crude residue was purified via preparative LCMS (XBridge C18 Column, eluting with a gradient of acetonitrile in water with 0.1% trifluoroacetic acid, at flow rate of 60 mL/min) to give the desired product (14.6 mg, 66.4%) as a yellow tinted solid. 1H NMR (400 MHz, DMSO-d6) delta 8.18 (s, 1H), 7.77 (d, J=2.1 Hz, 1H), 7.68-7.49 (m, 5H), 7.34 (d, J=8.2 Hz, 1H), 6.71 (d, J=2.0 Hz, 1H), 3.92 (s, 3H), 2.39 (s, 3H). LCMS for C18H18F3N6O2 (M+H)+: m/z=407.1; Found: 407.1.

Reference： [1]Patent: US2020/2295,2020,A1 .Location in patent: Paragraph 1407

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	945863-21-8	MDL No. :	MFCD08458483
Formula :	C₁₃H₁₉BN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LUMBLRWRRONQMO-UHFFFAOYSA-N
M.W :	262.11	Pubchem ID :	44119560
Synonyms :

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:

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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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Storage
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P401
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H400	Very toxic to aquatic life
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H402	Harmful to aquatic life
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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

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Quality Control of [ 945863-21-8 ]

Related Doc. of [ 945863-21-8 ]

Product Details of [ 945863-21-8 ]

Safety of [ 945863-21-8 ]

Application In Synthesis of [ 945863-21-8 ]

[ 945863-21-8 ] Synthesis Path-Upstream 1~1

[ 945863-21-8 ] Synthesis Path-Downstream 1~52

Related Functional Groups of
[ 945863-21-8 ]

Organoboron

Amides

Amines

Related Parent Nucleus of
[ 945863-21-8 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 945863-21-8 ] {[proInfo.proName]}

Quality Control of [ 945863-21-8 ]

Related Doc. of [ 945863-21-8 ]

Product Details of [ 945863-21-8 ]

Safety of [ 945863-21-8 ]

Application In Synthesis of [ 945863-21-8 ]

[ 945863-21-8 ] Synthesis Path-Upstream 1~1

[ 945863-21-8 ] Synthesis Path-Downstream 1~52

Related Functional Groups of [ 945863-21-8 ]

Organoboron

Amides

Amines

Related Parent Nucleus of [ 945863-21-8 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 945863-21-8 ]

Related Parent Nucleus of
[ 945863-21-8 ]