[ CAS No. 1025718-91-5 ]

Name: 1025718-91-5|Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate|95%
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Product Details of [ 1025718-91-5 ]

CAS No. :	1025718-91-5	MDL No. :	MFCD09027079
Formula :	C₁₃H₁₈BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	263.10 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 1025718-91-5 ]

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

Application In Synthesis of [ 1025718-91-5 ]

Downstream synthetic route of [ 1025718-91-5 ]

[ 1025718-91-5 ] Synthesis Path-Downstream 1~16

1
[ 29681-44-5 ]
[ 73183-34-3 ]
[ 1025718-91-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium acetate In N,N-dimethyl-formamide at 0 - 80℃; for 10h;	24.2 To the solution of 4,4,5,5-tetramethyl- 2-(4,4,5,5-tetramethyl (1,3.2 - dioxaborolan-2-yl)) -1,3,2-dioxaborolane (660mg, 2.60mmol) in DMF (1OmL) at O0C was added KOAc (638g, 6.50mmol) and Pd(dppf)Cl2.CH2Cl2 (53mg, 0.065mmol). The reaction mixture was heated to 8O0C at which point a solution of 24b (468mg, 2.17mmol) in DMF (1 OmL) was added drop- wise. The resulting mixture was stirred at 8O0C for 1 Oh more and evaporated. The residue was chromatographed on silica gel (EA:PE=l :10) to provide 24c (572mg, ca. 100%).
79.4%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 89.84℃; for 24h; Inert atmosphere;
66%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;	1.2 Synthesis of methyl 5-(4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)nicotinate To a solution of methyl 5-bromonicotinate (1 g, 4.6 mmol), KOAc (920 mg, 9.2 mmol) and (Bpin)2 (1.7 g, 6.9 mmol) in DMF (10 mE) was added Pd(dppf)C12 under N2, and the resulting reaction mixture was stirred for 4 h at 80°C. After the reaction mixture was concentrated,the residue was dissolved in DCM, then filtered, evaporated and the residue was purified by flash chromatography (PE / EtOAc = 4 / 1) to give the product of methyl 5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)nicotinate (800 mg, yield: 66%). ‘H-NMR (CDC13, 400 MHz) 9.21 (d, J= 2.4 Hz, 1H), 9.03 (d, J= 2.0 Hz, 1H), 8.61 (t, J= 2.0 Hz, 1H), 3.90 (s, 3H), 1.31 (s, 12H). MS (M+H):264.

66%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;	1.2 Step 2 - Synthesis of methyl 5-(4, 4,5, 5-tetramet hyl-1 , 3, 2-dioxaborolan-2-yl)nicotinate To a solution of methyl 5-bromonicotinate (1 g, 4.6 mmol), KOAc (920 mg, 9.2 mmol) and (Bpin)2 (1.7 g, 6.9 mmol) in DMF (10 mL) was added Pd(dppf)C12 under N2, and the resulting reaction mixture was stirred for 4 h at 80°C. After the reaction mixture was concentrated, the residue was dissolved in DCM, then filtered, evaporated and the residue was purified by flash chromatography (PE / EtOAc = 4 / 1) to give the product of methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (800 mg, yield: 66%). ‘H-NMR (CDC13, 400 MHz) 9.21 (d, J= 2.4 Hz, 1H), 9.03 (d, J= 2.0 Hz, 1H), 8.61 (t, J= 2.0 Hz, 1H), 3.90 (s, 3H),1.31 (s, 12H). MS (M+H): 264.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In dimethyl sulfoxide at 80℃; for 4h; Schlenk technique; Inert atmosphere;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate

Reference： [1]Current Patent Assignee: BETTA PHARMACEUTICALS CO LTD - WO2008/88881, 2008, A1 Location in patent: Page/Page column 49
[2]Zhou, Ping; Wang, Xinxin; Yue, Lianglan; Fan, Lihui; He, Yabing [Inorganic Chemistry, 2021, vol. 60, # 19, p. 14969 - 14977]
[3]Current Patent Assignee: MERCK & CO INC - WO2014/205592, 2014, A1 Location in patent: Page/Page column 30
[4]Current Patent Assignee: MERCK & CO INC - WO2014/209729, 2014, A1 Location in patent: Page/Page column 28
[5]Gràcia, Jordi; Buil, Maria Antonia; Castro, Jordi; Eichhorn, Peter; Ferrer, Manel; Gavaldà, Amadeu; Hernández, Begoña; Segarra, Victor; Lehner, Martin D.; Moreno, Imma; Pagès, Lluís; Roberts, Richard S.; Serrat, Jordi; Sevilla, Sara; Taltavull, Joan; Andrés, Miriam; Cabedo, Judit; Vilella, Dolors; Calama, Elena; Carcasona, Carla; Miralpeix, Montserrat [Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497]
[6]Fan, Lihui; He, Yabing; Wang, Xinxin; Yue, Lianglan; Zhou, Ping [Inorganic Chemistry, 2021, vol. 60, # 22, p. 17249 - 17257]

2
[ 1025718-91-5 ]
[ 1040376-44-0 ]
[ 1040377-10-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In water; N,N-dimethyl-formamide at 80℃;	24.3 To the solution of 24c (174mg, 0.66mmol) and D (lOOmg, 0.27mmol) in DMF (1 OmL) was added Pd(Ph3 )2C12 (18mg, 0.026mmol) under the protection of nitrogen, followed by IN Na2CO3 aq. (1.ImL) drop-wise. The reaction mixture was degassed with nitrogen, heated at 8O0C overnight and filtered. The filtrate was evaporated. The residue was dissolved in CH2Cl2/methanol (2:1), dried over Na2SO4, filtered and evaporated to afford crude product 24e which was used directly for the next reaction without further purification.

Reference： [1]Current Patent Assignee: BETTA PHARMACEUTICALS CO LTD - WO2008/88881, 2008, A1 Location in patent: Page/Page column 49

3
[ 1025718-91-5 ]
[ 1186111-63-6 ]
[ 1186111-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	97 Intermediate 97Methyl 6'-(3-ethylureido)-4'-(5-((2-methoxyethylamino)methyl)-4-(trifluoromethyl)thiazol-2- yl)-3,3'-brpyridine-5-carboxylate l-(5-bromo-4-(5-((2-methoxyethylamino)methyl)-4-(trifluoromethyl)thiazol-2-yl)pyridin-2- yl)-3 -ethylurea (Intermediate 90, -500 mg, 1 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)nicotinate (0.40 g, 1.5 mmol), and trans dichlorobis(triphenylphosphine)palladium (II) (70 mg, 0.1 mmol) were dissolved in 1,4- dioxane (10 mL). Sodium bicarbonate (252 mg, 3 mmol) was dissolved in water (3 mL) and added to the above mixture. The reaction was heated at 110°C in a microwave for 30 minutes. Ethyl acetate (10 mL) was then added to the reaction and the layers were separated. The solvent was removed in vacuo and the residue was chromatographed on a 12g Analogix column using 0-10% methanol in dichloromethane. The product containing fractions were combined to give the product ester (65% yield). MS (ESP): 539.1 (M+H+) for C23H25F3N6O4S 1H NMR (300 MHz, DMSO-d6): δ 1.11 (t, 3H), 3.21 (m, 2H), 3.23 (s, 3H), 3.37 (m, 4H), 3.89 (s, 3H), 7.49 (t, IH), 8.24 (IH), 8.28 (t, IH), 8.37 (s, IH), 8.74 (d, IH), 9.02 (t, IH), 9.11 (d, IH), 9.52 (bs, IH).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 285-286

4
[ 1025718-91-5 ]
[ 1186111-56-7 ]
[ 1186111-77-2 ]
[ 1186111-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	104; 105 Intermediate 104 and Intermediate 105 methyl 6'-(3-ethylureido)-4'-(5-(2-methoxyethylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)- 3,3'-bipyridine-5-carboxylate and 6'-(3-ethylureido)-4'-(5-(2-methoxyethylcarbamoyl)-4- (trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acid To a 35 mL microwave vial was added sequentially 2-(5-bromo-2-(3-ethylureido)pyridin-4- yl)-N-(2-methoxyethyl)-4-(trifluoromethyl)thiazole-5-carboxamide (Intermediate 83, 0.5 g, 1.0 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinate (0.40 g, 1.5 mmol), saturated sodium bicarbonate aqueous solution (3 mL), 1,4-dioxane (10 mL), and dichloro-bis(triphenylphosphino) palladium (II) (70 mg, 0.10 mmol). The mixture was then heated at 110 0C in a microwave for 30min. Ethyl acetate (40 mL) and water (40 mL) were added. The aqueous layer was then further extracted with ethyl acetate (2x, 5OmL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was loaded on 24g Analogix silica gel column [Heptanes: (9/1) ethyl acetate/methanol] to give ester (Intemediate 105) as off-white powder. The aqueous layer was adjusted to pH ~4 with dilute HCl and extracted with ethyl acetate /tetrahydrofuran (1/1) (3x, 10OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give crude acid Intermediate 106 as yellow solid which was used without further purification.Interemdiate 104: Methyl 6'-(3-ethylureido)-4'-(5-(2-methoxyethylcarbamoyl)-4- (trifluoromethyl) thiazol-2-yl)-3,3'-bipyridine-5-carboxylate MS (ESP): 553.2 (M+H+) for C23H23F3N6O5S1H NMR (300 MHz, DMSO-d6): δ 1.11 (t, 3H), 3.21 (m, 2H), 3.23 (s, 3H), 3.37 (m, 4H), 3.89 (s, 3H), 7.49 (t, IH), 8.24 (IH), 8.28 (t, IH), 8.37 (s, IH), 8.74 (d, IH), 9.02 (t, IH), 9.11 (d, IH), 9.52 (bs, IH).Intermediate 105: 6'-(3-ethylureido)-4'-(5-(2-methoxyethylcarbamoyl)-4- (trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acid MS (ESP): 539.1 (M+H+) for C22H21F3N6O5S

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 289-290

5
[ 1025718-91-5 ]
[ 1186111-57-8 ]
[ 1186111-79-4 ]
[ 1186111-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	106; 107 Intermediate 106 and Intermediate 107 methyl 6'-(3 -ethylureido)-4'-(5 -(2-morpholinoethylcarbamoyl)-4-(trifluoromethyl)thiazol-2- yl)-3,3'-bipyridine-5-carboxylate and 6'-(3-ethylureido)-4'-(5-(2-morpholinoethylcarbamoyl)- 4-(trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acid To a 35 mL microwave vial was added sequentially 2-(5-bromo-2-(3-ethylureido)pyridin-4- yl)-N-(2-morpholinoethyl)-4-(trifluoromethyl)thiazole-5-carboxamide (Intermediate 84, 0.5 g, 0.9 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinate (0.36 g, 1.4 mmol), saturated sodium bicarbonate aqueous solution (3 mL), 1,4-dioxane (10 mL), and dichloro-bis(triphenylphosphino) palladium (II) (65 mg, 0.09 mmol). The mixture was then heated to 110 0C in a microwave for 30min. Ethyl acetate (40 mL) and water (40 mL) were added. The aqueous layer was then further extracted with ethyl acetate (2x, 5OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give the crude ester (Intermediate 106) which was used without further purification. The aqueous layer was adjusted to pH ~4 with dilute HCl and extracted with ethyl acetate /tetrahydrofuran (1/1) (3 x, 10OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give crude acid Intermediate 107 as yellow solid which was also used without further purification.Intermediate 106: Methyl 6'-(3-ethylureido)-4'-(5-(2-morpholinoethylcarbamoyl)-4- (trifluoromethyl) thiazol-2-yl)-3,3'-bipyridine-5-carboxylate MS (ESP): 608.1 (M+H+) for C26H28F3N7O5SIntermediate 107: 6'-(3-ethylureido)-4'-(5-(2-morpholinoethylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acidMS (ESP): 594.0 (M+H+) for C25H26F3N7O5S

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 290-291

6
[ 1025718-91-5 ]
[ 1186111-58-9 ]
[ 1186111-81-8 ]
[ 1186111-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	108; 109 Intermediate 108 and Intermediate 109 methyl 6'-(3-ethylureido)-4'-(5-(2-(4-methylpiperazin-l-yl)ethylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylate and 6'-(3-ethylureido)-4'-(5-(2-(4- methylpiperazin-l-yl)ethylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5- carboxylic acid To a 35 niL microwave vial was added sequentially 2-(5-bromo-2-(3-ethylureido)pyridin-4- yl)-N-(2-(4-methylpiperazin-l-yl)ethyl)-4-(trifluoromethyl)thiazole-5-carboxamide (Intermediate 85, 0.5 g, 0.9 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)nicotinate (0.36 g, 1.4 mmol), saturated sodium bicarbonate aqueous solution (3 mL), 1,4- dioxane (10 mL), and dichloro-bis(triphenylphosphino) palladium (II) (65 mg, 0.09 mmol). The mixture was then heated to 110 0C in a microwave for 30min. Ethyl acetate (40 mL) and water (40 mL) were added. The aqueous layer was then further extracted with ethyl acetate (2x, 5OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give the crude ester (Intermediate 108) which was used for the next step without further purification. The aqueous layer was then adjusted to pH ~6, 4, and 2 with dilute HCl, and extracted with ethyl acetate /tetrahydrofuran (1/1) however the product remained in the aqueous layer. The aqueous layer was then passed through a 30g Analogix Cl 8 column (acetonitrile/water) to remove most of the salts and give acid Intermediate 109 as yellow solid which was used without further purification.Intermediate 108: Methyl 6'-(3-ethylureido)-4'-(5-(2-(4-methylpiperazin-l- yl)ethylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylate MS (ESP): 621.3 (M+H+) for C27H31F3N8O4SIntermediate 109: 6'-(3-ethylureido)-4'-(5-(2-(4-methylpiperazin-l-yl)ethylcarbamoyl)-4- (trifluoromethyl)thiazol-2-yl)-3,3'-bipyridine-5-carboxylic acid MS (ESP): 607.2 (M+H+) for C26H29F3N8O4S

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 290-291

7
[ 1025718-91-5 ]
[ 1186111-62-5 ]
[ 1186111-83-0 ]
[ 1186111-84-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	110; 111 Intermediate 110 and Intermediate 111 methyl 4'-(5-(cyclopropylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3-ethylureido)-3,3'- brpyridine-5-carboxylate and 4'-(5-(cvclopropylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3-ethvlureido)-3, S'-bipyridine-S-carboxylic acid To a 35 niL microwave vial was added sequentially 2-(5-bromo-2-(3-ethylureido)pyridin-4- yl)-N-cyclopropyl-4-(trifluoromethyl)thiazole-5-carboxamide (Intermediate 89, 0.5 g, 1.0 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinate (0.4 g, 1.5 mmol), saturated sodium bicarbonate aqueous solution (3 mL), 1,4-dioxane (10 mL), and dichloro- bis(triphenylphosphino) palladium (II) (70 mg, 0.1 mmol). The mixture was then heated to 110 0C in a microwave for 30min. Ethyl acetate (40 mL) and water (40 mL) were added. The aqueous layer was then further extracted with ethyl acetate (2x, 5OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give the crude ester (Intermediate 110) which was used without further purification. The aqueous layer was adjusted to pH ~4 with dilute HCl and extracted with ethyl acetate /tetrahydrofuran (1/1) (3 x, 10OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give acid Intermediate 111 as yellow solid which was also used without further purification.Intermediate 110: Methyl 4'-(5-(cyclopropylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'- (3-ethylureido)-3,3'-bipyridine-5-carboxylate MS (ESP): 535.2(M+H+) for C23H21F3N6O4SIntermediate 111: 4'-(5-(cyclopropylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3- ethylureido)-3,3'-bipyridine-5-carboxylic acid MS (ESP): 521.1 (M+H+) for C22H19F3N6O4S

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 292-293

8
[ 1025718-91-5 ]
[ 1186111-61-4 ]
[ 1186111-85-2 ]
[ 1186111-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	112; 113 Intermediate 112 and Intermediate 113 methyl 4'-(5-(cyclopentylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3-ethylureido)-3,3'- bipyridine-5-carboxylate and 4'-(5-(cyclopentylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)- 6'-(3-ethylureido)-3,3'-brpyridine-5-carboxylic acid To a 35 niL microwave vial was added sequentially 2-(5-bromo-2-(3-ethylureido)pyridin-4- yl)-N-cyclopentyl-4-(trifluoromethyl)thiazole-5-carboxamide (Intermediate 88, 0.5 g, 1.0 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinate (0.4 g, 1.5 mmol), saturated sodium bicarbonate aqueous solution (3 mL), 1,4-dioxane (10 mL), and dichloro- bis(triphenylphosphino) palladium (II) (70 mg, 0.1 mmol). The mixture was then heated to 110 0C in a microwave for 30min. Ethyl acetate (40 mL) and water (40 mL) were added. The aqueous layer was then further extracted with ethyl acetate (2x, 5OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give the crude ester (Intermediate 112) which was used without further purification. The aqueous layer was adjusted to pH ~4 with dilute HCl and extracted with ethyl acetate /tetrahydrofuran (1/1) (3 x, 10OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give crude acid Intermediate 113 as yellow solid which was also used without further purification.Intermediate 112: Methyl 4'-(5-(cyclopentylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'- (3-ethylureido)-3,3'-bipyridine-5-carboxylate MS (ESP): 563.1(M+H+) for C25H25F3N6O4SIntermediate 113: 4'-(5-(cyclopentylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3- ethylureido)-3,3'-bipyridine-5-carboxylic acid MS (ESP): 549.0 (M+H+) for C24H23F3N6O4S

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 294

9
[ 1025718-91-5 ]
[ 1186111-60-3 ]
[ 1186111-87-4 ]
[ 1186111-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; for 0.5h; Microwave irradiation;	114; 115 Intermediate 114 and Intermediate 115 methyl 4'-(5-(cyclohexylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3-ethylureido)-3,3'- bipyridine-5-carboxylate and 4'-(5-(cyclohexylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'- (3-ethylureido)-3,3'-brpyridine-5-carboxylic acid To a 35 niL microwave vial was added sequentially 2-(5-bromo-2-(3-ethylureido)pyridin-4- yl)-N-cyclohexyl-4-(trifluoromethyl)thiazole-5-carboxamide (Intermediate 87, 0.5 g, 1.0 mmol), methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinate (0.4 g, 1.5 mmol), saturated sodium bicarbonate aqueous solution (3 mL) 1,4-dioxane (10 mL), and dichloro- bis(triphenylphosphino) palladium (II) (70 mg, 0.1 mmol). The mixture was then heated to 110 0C in a microwave for 30min. Ethyl acetate (40 mL) and water (40 mL) were added. The aqueous layer was then further extracted with ethyl acetate (2x, 5OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give the crude ester (Intermediate 114) which was used without any further purification. The aqueous layer was adjusted to pH ~4 with dilute HCl and extracted with ethyl acetate /tetrahydrofuran (1/1) (3 x, 10OmL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give crude acid Intermediate 115 as yellow solid which was also used without further purification.Intermediate 114: Methyl 4'-(5-(cyclohexylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'- (3-ethylureido)-3,3'-bipyridine-5-carboxylate MS (ESP): 577.1(M+H+) for C26H27F3N6O4SIntermediate 115: 4'-(5-(cyclohexylcarbamoyl)-4-(trifluoromethyl)thiazol-2-yl)-6'-(3- ethylureido)-3,3'-bipyridine-5-carboxylic acid MS (ESP): 563.1 (M+H+) for C25H25F3N6O4S

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/106885, 2009, A1 Location in patent: Page/Page column 295

11
[ 1025718-91-5 ]
[ 4595-60-2 ]
[ 1237518-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; water for 1.5h; Reflux; Inert atmosphere;	22b Reference Example 22b; 2-Bromopyrimidine (73 mg), sodium carbonate (81 mg), water (0.3 mL), and bis(triphenylphosphine)palladium(II) dichloride (5.3 mg) were added to an ethylene glycol dimethyl ether (1 mL) solution of methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate (0.10 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. After cooling the reaction mixture to room temperature, ethyl acetate and water were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-50% hexane/ethyl acetate] to obtain 30 mg of methyl 5-(pyrimidin-2-yl)pyridine-3-carboxylate as a yellow solid.

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US2011/275797, 2011, A1 Location in patent: Page/Page column 52

12
[ 1025718-91-5 ]
[ 1237518-66-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 1.5 h / Reflux; Inert atmosphere 2.1: sodium hydroxide; water / 1,4-dioxane; methanol / 1.5 h / 20 °C 2.2: pH 3.8

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US2011/275797, 2011, A1

13
[ 887144-97-0 ]
[ 1025718-91-5 ]
[ 124236-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,10-Phenanthroline; lithium hydroxide monohydrate; copper(II) thiophene-2-carboxylate In dichloromethane at 45℃; Inert atmosphere; regioselective reaction;

Reference： [1]Liu, Tianfei; Shao, Xinxin; Wu, Yaming; Shen, Qilong [Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 540 - 543]

14
[ 93-60-7 ]
[ 73183-34-3 ]
[ 1025718-91-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: bis(pinacol)diborane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₅₁H₃₂N₈Zn In para-xylene at 20℃; for 0.5h; Schlenk technique; Stage #2: methyl 3-pyridinecarboxylate In para-xylene at 80℃; for 18h; Schlenk technique; regioselective reaction;
	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;
	With 2,6-di-tert-butyl-pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In tetrahydrofuran at 80℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;

Reference： [1]Al-Shehimy, Shaymaa; Gramage-Doria, Rafael; Roisnel, Thierry; Trouvé, Jonathan; Zardi, Paolo [Angewandte Chemie - International Edition, 2021, vol. 60, # 33, p. 18006 - 18013][Angew. Chem., 2021, vol. 133, # 33, p. 18154 - 18161]
[2]Liu, Tianfei; Shao, Xinxin; Wu, Yaming; Shen, Qilong [Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 540 - 543]
[3]Herbert, Simon; Kinzel, Tom; Shen, Qilong; Zhang, Wei; Zhao, Haiwei [Journal of Organic Chemistry, 2020, vol. 85, # 5, p. 3596 - 3604]

15
[ 1025718-91-5 ]
[ 1427587-99-2 ]
[ 1427588-01-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 120℃; for 3h;	32.C [C] 6-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3]bipyridinyl-5′-carboxylic acid methyl ester 3-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester (1.2 g, 2.7 mmol), Pd(PPh3)2Cl2 (190 mg, 0.27 mmol), Na2CO3 (572 mg, 5.4 mmol) and 3-(methoxycarbonyl)pyridine-5-boronic acid pinacol ester (926 mg, 3.5 mmol) were dissolved in 1,4-dioxane (4.0 mL) and the resulting reaction mixture was heated at 120° C. for 3 hours before it was poured into H2O (50 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 6-(2-methoxycarbonyl-vinyl)-5-nitro-[2,3′]bipyridinyl-5′-carboxylic acid methyl ester (926 mg, quant.) as a light yellow solid. MS: 344.1 (M+H+)
100%	With sodium carbonate In 1,4-dioxane at 120℃; for 3h;	32.C [C] 6-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3^,]bipyridinyl-5'-carboxylic acid methyl ester [C] 6-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3,]bipyridinyl-5'-carboxylic acid methyl ester 3-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester (1.2 g, 2.7 mmol), Pd(PPh3)2Cl2 (190 mg, 0.27 mmol), Na2C03 (572 mg, 5.4 mmol) and 3- (methoxycarbonyl)pyridine-5-boronic acid pinacol ester (926 mg, 3.5 mmol) were dissolved in 1,4-dioxane (4.0 mL) and the resulting reaction mixture was heated at 120 °C for 3 hours before it was poured into H20 (50 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give 6-(2-methoxycarbonyl-vinyl)-5-nitro-[2,3']bipyridinyl-5'-carboxylic acid methyl ester (926 mg, quant.) as a light yellow solid. MS: 344.1 (M+H+).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2013/72679, 2013, A1 Location in patent: Paragraph 0745; 0746
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2013/37779, 2013, A1 Location in patent: Page/Page column 130; 131

16
[ 1025718-91-5 ]
[ 1427588-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate / 1,4-dioxane / 3 h / 120 °C 2: acetic acid; palladium 10% on activated carbon; hydrogen / methanol / 13 h / 50 °C / 2585.81 Torr
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,4-dioxane / 3 h / 120 °C 2: palladium 10% on activated carbon; hydrogen; acetic acid / methanol / 13 h / 50 °C / 2585.81 Torr

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2013/37779, 2013, A1
[2]Current Patent Assignee: ROCHE HOLDING AG - US2013/72679, 2013, A1

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[ CAS No. 1025718-91-5 ]

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[ 1025718-91-5 ] Synthesis Path-Downstream 1~16

Related Functional Groups of [ 1025718-91-5 ]

Organoboron

Esters

Related Parent Nucleus of [ 1025718-91-5 ]

Pyridines

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[ 1025718-91-5 ]

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[ 1025718-91-5 ]