957061-12-0|Methyl 3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate| Ambeed

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Quality Control of [ 957061-12-0 ] Purity: 98% SDS Specification

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Product Details of [ 957061-12-0 ]

CAS No. :	957061-12-0
Formula :	C₁₄H₁₈BNO₆
M.W :	307.11
SMILES Code :	O=C(OC)C1=CC(B2OC(C)(C)C(C)(C)O2)=CC([N+]([O-])=O)=C1
MDL No. :	MFCD09258774
InChI Key :	KSHZAKDFKZEZJQ-UHFFFAOYSA-N
Pubchem ID :	44119765

Safety of [ 957061-12-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 957061-12-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 957061-12-0 ]

[ 957061-12-0 ] Synthesis Path-Downstream 1~12

1
[ 50765-19-0 ]
[ 73183-34-3 ]
[ 957061-12-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium acetate;PdCl2(dpf)2; In dimethyl sulfoxide; at 80.0℃; for 2.0h;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester To a stirred solution of 3-Iodo-5-nitro-benzoic acid methyl ester (5.0 g, 0.016 mol), bis(pinacolato)diborane (4.55 g, 0.018 mol) and KOAc (4.80 g, 0.049 mol) in DMSO (50 mL) was added PdCl2(dpf)2 (0.40 g, 0.50 mmol). The mixture was flushed with N2 and heated to 80 C. for 2 h. After the reaction mixture was cooled down to room temperature, H2O (20 mL) was added and the mixture was extracted with Et2O (3*30 mL). The organic layer was separated and washed with H2O, brine and dried over Na2SO4. Solvent was removed and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester as a white solid (3.30 g, 67%) MS (M+H)=308.
67%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 2.0h;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic Acid Methyl Ester; To a stirred solution of 3-Iodo-5-nitro-benzoic acid methyl ester (5.0 g, 0.016 mol), bis(pinacolato)diborane (4.55 g, 0.018 mol) and KOAc (4.80 g, 0.049 mol) in DMSO (50 mL) was added PdCl2(dpf)2 (0.40 g, 0.50 mmol). The mixture was flushed with N2 and heated to 80 C for 2 h. After the reaction mixture was cooled down to room temperature, H2O (20 mL) was added and the mixture was extracted with Et2O (3×30 mL). The organic layer was separated and washed with H2O, brine and dried over Na2SO4. Solvent was removed and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester as a white solid (3.30 g, 67%) MS (M+H)=308.
67%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80.0℃; for 2.0h;Inert atmosphere;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester To a stirred solution of 3-Iodo-5-nitro-benzoic acid methyl ester (5.0 g, 0.016 mol), bis(pinacolato)diborane (4.55 g, 0.018 mol) and KOAc (4.80 g, 0.049 mol) in DMSO (50 mL) was added PdCl2(dpf)2 (0.40 g, 0.50 mmol). The mixture was flushed with N2 and heated to 80 C for 2 h. After the reaction mixture was cooled down to room temperature, H2O (20 mL) was added and the mixture was extracted with Et2O (3×30 mL). The organic layer was separated and washed with H2O, brine and dried over Na2SO4. Solvent was removed and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester as a white solid (3.30 g, 67%) MS (M+H)=308.

	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[ 1,3,21 dioxaborolan-2-yl) -benzoic acid methyl ester; A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinaco- lato)diboron (9.1 g, 0.0358 mol), KOAc (9.5 9g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 800C for 4 h under N2 atmosphere. The mixture was cooled to RT and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO/t. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[ 1,3,2] dioxaborolan-2- yl) -benzoic acid methyl ester was used without purification in the next step.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic Acid Methyl Ester; A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.59 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic Acid Methyl Ester A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.5 9 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.59 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;Inert atmosphere;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.5 9 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;Inert atmosphere;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl esterA solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.5 9 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;Inert atmosphere;	Step 2 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.5 9 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.

References: [1]Patent: US2008/4442,2008,A1 .Location in patent: Page/Page column 194.
[2]Patent: US2009/163502,2009,A1 .Location in patent: Page/Page column 37.
[3]Patent: US2015/191487,2015,A1 .Location in patent: Paragraph 0625.
[4]Patent: WO2008/55840,2008,A1 .Location in patent: Page/Page column 56.
[5]Patent: US2009/163499,2009,A1 .Location in patent: Page/Page column 32.
[6]Patent: US2009/170873,2009,A1 .Location in patent: Page/Page column 46-47.
[7]Patent: US2009/170874,2009,A1 .Location in patent: Page/Page column 62-63.
[8]Patent: US2010/152203,2010,A1 .Location in patent: Page/Page column 23.
[9]Patent: US2010/324069,2010,A1 .Location in patent: Page/Page column 26-27.
[10]Patent: US2012/22067,2012,A1 .Location in patent: Page/Page column 35-36.

2
[ 3510-66-5 ]
[ 957061-12-0 ]
[ 1000587-40-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,1-dimethoxyethylene; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130 C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.
56%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic Acid Methyl Ester; To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130 C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.
56%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130 C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.

40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester; EPO <DP n="58"/>To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5ml/ ImI) was added 3-nitro-5- (4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 1300C for 0.5 h. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2ZMeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic Acid Methyl Ester; To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Microwave heating;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate; In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
40%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave radiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 3 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl esterTo a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4 (226 mg, 0.2 mmol) and K3PO4 (2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130 C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).

References: [1]Patent: US2008/4442,2008,A1 .Location in patent: Page/Page column 194.
[2]Patent: US2009/163502,2009,A1 .Location in patent: Page/Page column 37-38.
[3]Patent: US2015/191487,2015,A1 .Location in patent: Paragraph 0626.
[4]Patent: WO2008/55840,2008,A1 .Location in patent: Page/Page column 56-57.
[5]Patent: US2009/163499,2009,A1 .Location in patent: Page/Page column 32.
[6]Patent: US2009/170873,2009,A1 .Location in patent: Page/Page column 47.
[7]Patent: US2009/170874,2009,A1 .Location in patent: Page/Page column 62-63.
[8]Patent: US2010/152203,2010,A1 .Location in patent: Page/Page column 23.
[9]Patent: US2012/22067,2012,A1 .Location in patent: Page/Page column 36.
[10]Patent: US2010/324069,2010,A1 .Location in patent: Page/Page column 27.
[11]Patent: US2010/324056,2010,A1 .Location in patent: Page/Page column 33-34.

3
[ 73183-34-3 ]
[ 957061-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 4.0h;Inert atmosphere;	A solution of 3-iodo-5-nitro-benzoic acid methyl ester (10 g, 0.0326 mol), bis(pinacolato)diboron (9.1 g, 0.0358 mol), KOAc (9.5 9 g, 0.098 mol) and PdCl2(dppf) (798 mg, 0.98 mmol) in DMSO (40 ml) was heated to 80 C. for 4 hours under N2 atmosphere. The mixture was cooled to room temperature and extracted with Et2O. The combined organic phases were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the resulting crude 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester was used without purification in the next step.

References: [1]Patent: US2010/324056,2010,A1 .Location in patent: Page/Page column 33.

4
[ 121-92-6 ]
[ 957061-12-0 ]

References: [1]Patent: US2012/22067,2012,A1 .
[2]Patent: US2015/191487,2015,A1 .

5
[ 6313-17-3 ]
[ 957061-12-0 ]

References: [1]Patent: US2012/22067,2012,A1 .
[2]Patent: US2015/191487,2015,A1 .

6
[ 957061-12-0 ]
[ 1000587-41-6 ]

References: [1]Patent: US2012/22067,2012,A1 .
[2]Patent: US2015/191487,2015,A1 .

7
[ 957061-12-0 ]
[ 1000587-70-1 ]