[ CAS No. 532391-31-4 ]

Name: 532391-31-4|2-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|98%
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Quality Control of [ 532391-31-4 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 532391-31-4 ]

Product Details of [ 532391-31-4 ]

CAS No. :	532391-31-4	MDL No. :	MFCD05663507
Formula :	C₁₂H₁₈BNO₃	Boiling Point :	329.4°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	235.09 g/mol	Pubchem ID :	17750166
Synonyms :

Safety of [ 532391-31-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 532391-31-4 ]

Upstream synthesis route of [ 532391-31-4 ]
Downstream synthetic route of [ 532391-31-4 ]

[ 532391-31-4 ] Synthesis Path-Upstream 1~1

1
[ 76-09-5 ]
[ 163105-90-6 ]
[ 532391-31-4 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 6, p. 1346 - 1349

[ 532391-31-4 ] Synthesis Path-Downstream 1~11

1
[ 105130-25-4 ]
[ 532391-31-4 ]
[ 1231925-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In 1,2-dimethoxyethane; water; at 100℃; for 0.25h;Microwave irradiation;	STEP 2. 4-(3-(2-METHOXYPYRIDIN-3-YL)PYRAZIN-2-YLOXY)ANILINE To a glass microwave vial was added 4-(3-chloropyrazin-2-yloxy)aniline (1.0591 g, 4.78 mmol), <strong>[532391-31-4]2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine</strong> hydrate, trans-dichlorobis(triphenylphosphine) palladium (II) (0.268 g, 0.382 mmol), and sodium carbonate (2.53 g, 23.89 mmol) in DME (7.65 mL) and water (1.911 mL). The reaction mixture was stirred and heated in a Biotage Initiator microwave reactor at 100 C. for 15 min. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide 4(3-(2-methoxypyridin-3-yl)pyrazin-2-yloxy)aniline. MS (ESI, pos. ion) m/z:295.2.

Reference： [1]Patent: US2010/160280,2010,A1 .Location in patent: Page/Page column 118; 119

2
[ 532391-31-4 ]
[ 133038-74-1 ]
[ 1426414-41-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1346 - 1349

3
[ 76-09-5 ]
[ 163105-90-6 ]
[ 532391-31-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1346 - 1349

4
[ 532391-31-4 ]
[ 1426414-44-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1346 - 1349

5
[ 532391-31-4 ]
[ 1426414-55-2 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1346 - 1349

6
[ 532391-31-4 ]
4-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]
[ 76-05-1 ]
N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-(2-methoxypyridin-3-yl)-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Example 61A N-alpha-[(trans-4-[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-(2-methoxypyridin-3-yl)-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide 250 mg (0.40 mmol) of 4-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}-cyclohexyl)carbonyl]-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide and 46 mg (0.04 mmol) of tetrakis(triphenylphosphine)palladium(0) were taken up in 3.6 ml of 1,2-dimethoxyethane under argon and stirred at RT for 10 min. A solution of 281 mg (1.20 mmol) of <strong>[532391-31-4]2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine</strong> in 1.35 ml of ethanol was added dropwise to the reaction mixture, which was stirred at RT for a further 10 min. After the addition of 3 ml of 2N aqueous sodium carbonate solution, the mixture was stirred at RT for 5 min and under reflux for 3 h. The reaction mixture was dissolved in a little methanol/acetonitrile, filtered through a Millipore syringe filter and separated by preparative HPLC (mobile phase: acetonitrile/water gradient). This gave 217 mg (82% of theory) of the title compound. LC-MS (Method 1): Rt=1.07 min; MS (ESIneg): m/z=653 [M-H]-.

Reference： [1]Patent: US2016/280699,2016,A1 .Location in patent: Paragraph 0615; 0616; 0617

7
[ 532391-31-4 ]
[ 1765-93-1 ]
[ 174913-12-3 ]
3-(4'-fluoro-5-methoxy-[1,1'-biphenyl]-3-yl)-2-methoxypyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1249 - 1253
Angew. Chem.,2017,p. 1269 - 1273,5

8
[ 532391-31-4 ]
α-cumyl bromodifluoromethanesulfenate [ No CAS ]
3-((bromodifluoromethyl)thio)-2-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With [(1,2-bis(diphenylphosphino)ethane)CuCl]; sodium t-butanolate; In toluene; at 50℃; for 2h;Glovebox; Sealed tube;	In the glove box, the DPPECuCl (25 mg, 10 muM %) and NaOt Bu (15 mg, 30 muM %) is added to the in tube sealing, and then adding 3-(boronic acid pinacol ester)-2-methoxy pyridine (0.5 mmol, 1.0 equiv, 118 mg) and compound I-1 (0.6 mmol, 1.2 equiv, 178 mg), 2 ml toluene, 50 C stirring 2 h. After the reaction, steaming and under reduced pressure, the residue passes through the rapid silica gel column chromatography, to obtain yellowish liquid 112 mg, yield 83%. After hydrogen spectrum identifying the purity of greater than 95%.

Reference： [1]Patent: CN107011219,2017,A .Location in patent: Paragraph 0132-0134
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 2413 - 2417
Angew. Chem.,2019,vol. 131,p. 2435 - 2439,5

9
[ 532391-31-4 ]
7-((1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-5-iodo-2-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
7-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-5-(2-methoxypyridin-3-yl)-2-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31.31%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 90℃; for 6h;	To a stirred solution of 7-[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-ylmethyl]-5-iodo-2-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (Preparation 54, 150.0 mg, 0.334 mmol) in EtOH-water (4:1) (8.0 mL) was added <strong>[532391-31-4]2-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine</strong> (153.2 mg, 1.002 mmol) and Na2CO3 (106.16 mg, 1.002 mmol). The reaction mixture was degassed with Ar for 15 min and Pd(PPh3)4 (38.6 mg, 0.033 mmol) added and degassed with Ar for 5 min and heated to 90 C. for 6 h. The reaction mixture was filtered through Celite washing through with 5% MeOH/DCM. The combined organics were evaporated to dryness under reduced pressure and the residue azeotroped with toluene. The solid was triturated with Et2O and purified by prep TLC (3% MeOH:DCM) to afford the title compound as an off white solid (45.0 mg, 31.31%). 1HNMR (400 MHz, MeOD-d4) 2.53 (s, 3H), 3.92 (s, 3H), 5.59 (s, 2H), 7.03 (dd, 1H), 7.24 (s, 1H), 7.38 (m, 2H), 7.54 (m, 1H), 7.67 (dd, 1H), 7.81 (t, 1H), 8.14 (dd, 1H), 8.37 (d, 1H). LCMS m/z=431[MH]+

Reference： [1]Patent: US2018/141954,2018,A1 .Location in patent: Paragraph 0708; 0709

10
[ 532391-31-4 ]
[ 74-88-4 ]
[ 19230-59-2 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 1337 - 1341

11
[ 532391-31-4 ]
(S,E)-tert-butyl (1-(4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1Himidazol-2-yl)-7-(isoxazol-3-yl)-7-oxohept-3-en-1-yl)carbamate [ No CAS ]
(S)-tert-butyl (7-(isoxazol-3-yl)-1-(4-(2-methoxypyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-7-oxohept-3-en-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; (2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1 ?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; In 1,4-dioxane; water; at 20 - 100℃; for 2h;Inert atmosphere;	XPhos Pd G3 (10 mg, 0.012 mmol) was added to a mixture of (S)-tert-butyl (l-(4- bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazol-2-yl)-7-(isoxazol-3-yl)-7-oxohept-3- en-l-yl)carbamate (17, 106 mg, 0.186 mmol), 2-methoxy-3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridine (110 mg, 0.468 mmol) and K3PO4 (123 mg, 0.579 mmol) in co solvents of dioxane (1.5 ml) and water (0.15 ml) at rt and the mixture was stirred at l00C for 2 h under N2 protection. The mixture was cooled, diluted with water (15 mL), and extracted with ethyl acetate (3 x 8 mL). The combined organic fractions were washed with brine (saturated, 8 mL), dried (Na2S04), filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column flash chromatography, eluting with petroleum ether / EtOAc = 0-50% to give (S)-tert-butyl (7-(isoxazol-3-yl)-l-(4-(2-methoxypyridin-3-yl)-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazol-2-yl)-7-oxohept-3-en-l-yl)carbamate (33 A). LCMS (ESI) calc?d for C3oH43N506Si [M+H]+: 598.3, found: 598.2

Reference： [1]Patent: WO2020/28150,2020,A1 .Location in patent: Page/Page column 81

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[ 532391-31-4 ]

Organoboron

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[ 532391-31-4 ]

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[ CAS No. 532391-31-4 ]

Quality Control of [ 532391-31-4 ]

Related Doc. of [ 532391-31-4 ]

Product Details of [ 532391-31-4 ]

Safety of [ 532391-31-4 ]

Application In Synthesis of [ 532391-31-4 ]

[ 532391-31-4 ] Synthesis Path-Upstream 1~1

[ 532391-31-4 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 532391-31-4 ]

Organoboron

Ethers

Related Parent Nucleus of [ 532391-31-4 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 532391-31-4 ]

Related Parent Nucleus of
[ 532391-31-4 ]