1350377-66-0|3-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline| Ambeed

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Quality Control of [ 1350377-66-0 ] Purity: 97% SDS Specification

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Product Details of [ 1350377-66-0 ]

CAS No. :	1350377-66-0
Formula :	C₁₃H₂₀BNO₃
M.W :	249.11
SMILES Code :	NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C(OC)=C1
MDL No. :	MFCD22494808
InChI Key :	ZYFRJTZQMFNEHS-UHFFFAOYSA-N
Pubchem ID :	67003693

Safety of [ 1350377-66-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1350377-66-0 ]

* 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 [ 1350377-66-0 ]

[ 1350377-66-0 ] Synthesis Path-Downstream 1~12

Yield	Reaction Conditions	Operation in experiment
	With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 95℃;Inert atmosphere;	General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+.
	With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 95℃;Inert atmosphere;	General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2+ H]+.
	With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 95℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+.

	With anhydrous potassium acetate; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 95℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2+ H]+
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous potassium acetate; triethylamine; at 90℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under aigon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl fe/7-butyl ether (4 x 250 mL). The filtrate was washed with water (2 * 500 mL) and brine (2 * 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+.
		General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+.
		General procedure: To a stirred solution of tricyclohexylphosphine (7.18 g, 25.7 mmol) in 1,4-dioxane (1.2 L) under argon atmosphere were added bis(pinacolato)diboron (89.62 g, 352.9 mmol) and potassium acetate (62.98 g, 641.7 mmol), followed by 4-bromo-3-methylaniline (A-1.1, 60.00 g, 320.8 mmol). The reaction mixture was purged with argon for 10 min. Palladium(II) acetate (5.77 g, 25.7 mmol) was added, and the mixture was purged with argon for 10 min. The reaction mixture was heated at 95 C with stirring for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, passed through a bed of diatomaceous earth, and washed with methyl tert-butyl ether (4 × 250 mL). The filtrate was washed with water (2 × 500 mL) and brine (2 × 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10% ethyl acetate/hexanes) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A-2.1, 44.80 g, yield: 60%) as a pale brown solid: ESI (m/z) 234 [C13H20BNO2 + H]+.

2
[ 352528-01-9 ]
[ 1350377-66-0 ]
[ 1430720-06-1 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3531 - 3545.

3
[ 849217-48-7 ]
[ 1350377-66-0 ]
N-(4-(3-amino-1H-indazol-4-yl)-3-methoxyphenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 564 - 578.

4
[ 849217-48-7 ]
[ 1350377-66-0 ]
C₂₄H₂₈BFN₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 0 - 20℃;	General procedure: To a mixture of 6d (40 mg, 0.178 mmol) and 7 (40 mg, 0.178 mmol) dissolved in 3 mL of DCM in ice-bath, HATU (122 mg, 0.320 mmol) was added. After stirring for 10 min, TEA (25 μL, 0.178 mmol) was dropped. The reaction was warmed to the room temperature and stirred overnight. After the completion of the reaction, the mixture was diluted with DCM (40 mL) and washed with water (3 * 20 mL) followed by brine (20 mL), dried over sodium sulfate, filtered, and evaporated. The crude product was purified by chromatograph (0-3% MeOH/DCM) to give the title compound 8d as a white solid (55 mg, 72%).

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 564 - 578.

5
[ 1350377-66-0 ]
(R)-N-(3-methoxy-4-(4-((1-phenylethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)methanesulfonamide [ No CAS ]