[ CAS No. 163105-90-6 ] {[proInfo.proName]}

Name: 163105-90-6|2-Methoxy-3-pyridineboronic acid|98%
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SKU: A145477
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Quality Control of [ 163105-90-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 163105-90-6 ]

Product Details of [ 163105-90-6 ]

CAS No. :	163105-90-6	MDL No. :	MFCD03411572
Formula :	C₆H₈BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVOLYUXUHWBCRJ-UHFFFAOYSA-N
M.W :	152.94	Pubchem ID :	2762709
Synonyms :

Calculated chemistry of [ 163105-90-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.55
TPSA :	62.58 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.06
Log Po/w (WLOGP) :	-1.23
Log Po/w (MLOGP) :	-1.19
Log Po/w (SILICOS-IT) :	-1.22
Consensus Log Po/w :	-0.72

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.1
Solubility :	12.2 mg/ml ; 0.0799 mol/l
Class :	Very soluble
Log S (Ali) :	-0.93
Solubility :	18.1 mg/ml ; 0.118 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.03
Solubility :	14.4 mg/ml ; 0.094 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 163105-90-6 ]

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:

Application In Synthesis of [ 163105-90-6 ]

* 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.

Upstream synthesis route of [ 163105-90-6 ]
Downstream synthetic route of [ 163105-90-6 ]

[ 163105-90-6 ] Synthesis Path-Upstream 1~7

1
[ 163105-90-6 ]
[ 13472-83-8 ]

Reference： [1] Chemical Science, 2017, vol. 8, # 2, p. 1551 - 1559

2
[ 2926-29-6 ]
[ 163105-90-6 ]
[ 121643-44-5 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 19, p. 4979 - 4981,3
[2] Organic Letters, 2012, vol. 14, # 19, p. 4979 - 4981

3
[ 50-00-0 ]
[ 163105-90-6 ]
[ 112197-16-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis(η3-allyl-μ-chloropalladium(II)); 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-4,5-dihydroimidazolinium chloride In tetrahydrofuran; water at 100℃; for 2 h; Inert atmosphere; Sealed tube	General procedure: [PdCl(η³-allyl)]₂ (0.00125-0.005 mmol), imidazolinium salt 1a (0.0025-0.01 mmol), arylboronic acid (0.50 mmol) and an inorganic base (2.0 mmol) were charged in a 10 mL test tube sealed with a rubber septum. The test tube was evacuated and backfilled with argon. This sequence was repeated five times. Then solvent (0.5 mL) and 37 wt percent formaldehyde in H₂O (102 mg, formaldehyde 1.25 mmol) were added via the rubber septum with syringe. In anargon flow, the rubber septum was replaced with a Teflon liners crew cap. The test tube was placed in an oil bath preheated at 100 C. The reaction mixture was stirred for 2 h and was cooled to room temperature. Then, operation of (i) or (ii) was performed. (i)The obtained crude was purified by passing it through a silica gel column with a hexane/ethyl acetate eluent (Table 4 entry 2 and Table 5 entries 8-16). (ii) Diphenylmethane (84.1 mg, 0.50 mmol) as an internal standard was added and then an aliquot of the organic layer of the reaction mixture was subjected to the quantitative analysis by 1H NMR (Table 4).

Reference： [1] Tetrahedron, 2014, vol. 71, # 1, p. 19 - 26

4
[ 1628-89-3 ]
[ 163105-90-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: With trimethylsilylmethyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 7 h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -20 - 20℃; for 0.666667 h;	A mixture of 2-methoxypyridine (23.2 g) and DIISOPROPYLAMINE (1.35 mL) in THF (223 mL) was added to (trimethylsilylmethyl) lithium (218 mL, 13.8 weight percent in hexanes) AT-20 °C. The lithiation was 84percent complete after 7 hours. Tri-isopropylborate (40.8 g) was added at-20 °C over 40 minutes. The mixture was stirred overnight at ambient temperature. 5 percent NAOH (aq, 225 mL) was added. The aqueous layer was removed and brought to pH 5 by adding 10percent HC1 (aq). The resulting white precipitate was isolated by filtration. After drying, 22.23 g of 2-methoxypyridine-3-boronic acid was obtained (68percent yield).

Reference： [1] Patent: WO2004/92125, 2004, A2, . Location in patent: Page 8
[2] Journal of Organic Chemistry, 2005, vol. 70, # 1, p. 388 - 390
[3] Synthesis, 2003, # 7, p. 1035 - 1038

5
[ 13472-59-8 ]
[ 163105-90-6 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481

6
[ 112197-15-6 ]
[ 163105-90-6 ]

Reference： [1] Patent: US2006/111394, 2006, A1, . Location in patent: Page/Page column 17

7
[ 76-09-5 ]
[ 163105-90-6 ]
[ 532391-31-4 ]

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

[ 163105-90-6 ] Synthesis Path-Downstream 1~26

1
[ 1628-89-3 ]
[ 163105-90-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		A mixture of <strong>[1628-89-3]2-<strong>[1628-89-3]methoxypyridine</strong></strong> (23.2 g) and DIISOPROPYLAMINE (1.35 mL) in THF (223 mL) was added to (trimethylsilylmethyl) lithium (218 mL, 13.8 weight percent in hexanes) AT-20 C. The lithiation was 84% complete after 7 hours. Tri-isopropylborate (40.8 g) was added at-20 C over 40 minutes. The mixture was stirred overnight at ambient temperature. 5 percent NAOH (aq, 225 mL) was added. The aqueous layer was removed and brought to pH 5 by adding 10% HC1 (aq). The resulting white precipitate was isolated by filtration. After drying, 22.23 g of <strong>[1628-89-3]2-<strong>[1628-89-3]methoxypyridine</strong></strong>-3-boronic acid was obtained (68% yield).

Reference： [1]Patent: WO2004/92125,2004,A2 .Location in patent: Page 8
[2]Journal of Organic Chemistry,2005,vol. 70,p. 388 - 390
[3]Synthesis,2003,p. 1035 - 1038

2
[ 6298-19-7 ]
[ 163105-90-6 ]
[ 835876-06-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium phosphate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;
69%	With sodium carbonate In 1,4-dioxane; water for 8h; Heating;

Reference： [1]Kudo, Noriaki; Perseghini, Mauro; Fu, Gregory C. [Angewandte Chemie - International Edition, 2006, vol. 45, # 8, p. 1282 - 1284]
[2]Thompson, Amy E.; Hughes, Gregory; Batsanov, Andrei S.; Bryce, Martin R.; Parry, Paul R.; Tarbit, Brian [Journal of Organic Chemistry, 2005, vol. 70, # 1, p. 388 - 390]

3
[ 42753-71-9 ]
[ 163105-90-6 ]
2'-methoxy-2-methyl[3,3']bipyridinyl-6-ylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 388 - 390

4
[ 6945-68-2 ]
[ 163105-90-6 ]
2'-methoxy-5-nitro[3,3']bipyridinyl-6-ylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 388 - 390

5
[ 112197-15-6 ]
[ 163105-90-6 ]

Yield	Reaction Conditions	Operation in experiment
		3-Iodo-2-methoxypyridine (3.0 g, 12.8 mmol) in anhydrous tetrahydrofuran (42 ml) was treated with triisopropyl borate (3.7 ml, 16 mmol) cooled to -100 C. in a liquid nitrogen/diethyl ether bath. To the cooled flask was added N-butyllithium/hexanes (10 ml, 16 mmol) dropwise via syringe. The solution was stirred for 90 minutes, warmed to room temperature, and stirred overnight. The reaction was quenched with 1N HCl (52 ml), stirred for 1 hour and neutralized to pH 8 with 50% NaOH. The basic solution was extracted with ethyl acetate (4×50 ml) and the combined organic extracts dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield the product as a brown oil. Chromatography (SiO2, 125 g, 1:9 ethyl acetate/hexanes) afforded the pure product as a white solid (0.225 g): 1H NMR (d6-DMSO, 300 MHz) delta 8.19 (dd, 1H, J=2.2, 5.1 Hz), 7.88 (m, 3H), 6.97 (dd, 1H, J=5.1, 7.0 Hz), 3.87 (s, 3H).

Reference： [1]Patent: US2006/111394,2006,A1 .Location in patent: Page/Page column 17

6
[ 578729-21-2 ]
[ 163105-90-6 ]
[ 943152-60-1 ]

Yield	Reaction Conditions	Operation in experiment
83.5%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 16h;	(R)-4-Bromo-thiophene-3-sulfonic acid {1-[4-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-amide 2M Aqueous sodium carbonate solution (3.25 ml, 6.50 mmol) was added to a mixture of 2-methoxypyridine-3-boronic acid (994 mg, 6.50 mmol), <strong>[578729-21-2](R)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester</strong> (650 mg, 2.16 mmol) and tetrakis(triphenylphosphine)palladium (0) (125 mg, 0.108 mmol) in 1,2 dimethoxyethane (27 ml). The mixture was heated at 95 C. for 16 h under nitrogen atmosphere. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed twice with brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The resulting gum was chromatographed over silica gel eluting with heptane/dichloromethane and the solvent evaporated to give (R)-{1-[4-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (593 mg, 1.71 mmol, 83.5%) as a crystalline solid. Trifluoroacetic acid (6.45 ml, 86.8 mmol) was added dropwise to a solution of (R)-{1-[4-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}carbamic acid tert-butyl ester (645 mg, 1.97 mmol) in dichloromethane (6.45 ml) under a nitrogen atmosphere at 0 C. After stirring for 1 h at 0 C. the solvent was evaporated. Methanol (20 ml) was added and the mixture added to a Strata 5 g/20 ml SCX column. The intermediate amine was eluted with 2M ammonia in methanol. The solvent was evaporated to give (R)-1-[4-(2-methoxy-pyridin-3-yl)-phenyl]-ethylamine as a gum (425 mg, 1.86 mmol, 94.6%). The title compound was then prepared in a similar manner to (R)-2,5-dimethyl-furan-3-sulfonic acid [1-(5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide (Example 10) using 4-bromo-3-thiophenesulfonyl chloride and 1-[4-(2-Methoxy-pyridin-3-yl)-phenyl]-ethylamine. Title compound: 1H NMR (400 MHz, CDCl3): delta 8.17 (d, 1H), 7.56 (d,1H), 7.41, 7.20 (a/b, 4H), 7.38 (m, 1H), 6.99-6.92 (m, 2H), 5.27 (d, 1H), 4.60 (m, 1H), 3.97 (s, 3H), 1.54 (d, 3H) ppm; MS (ESI) m/z: 453 [M+H]+.

Reference： [1]Patent: US2007/149577,2007,A1 .Location in patent: Page/Page column 7

7
[ 153034-91-4 ]
[ 163105-90-6 ]
[ 1206906-06-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane for 20h; Inert atmosphere; Reflux; regiospecific reaction;

Reference： [1]Location in patent: experimental part Daykin, Laura M.; Siddle, Jamie S.; Ankers, Adrian L.; Batsanov, Andrei S.; Bryce, Martin R. [Tetrahedron, 2010, vol. 66, # 3, p. 668 - 675]

8
[ 153034-91-4 ]
[ 163105-90-6 ]
[ 1206906-02-6 ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,4-dioxane for 24h; Reflux; Inert atmosphere; regiospecific reaction;

Reference： [1]Daykin, Laura M.; Siddle, Jamie S.; Ankers, Adrian L.; Batsanov, Andrei S.; Bryce, Martin R. [Tetrahedron, 2010, vol. 66, # 3, p. 668 - 675]

9
[ 1244041-71-1 ]
[ 163105-90-6 ]
[ 1244041-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride In 1,4-dioxane; water at 90℃; for 3h;	101.2 Step 2) Formation of tert-butyl [6-(2-methoxypyridin-3-yl)-1 ,3-benzothiazol-2- yljcarbamateA mixture of fe/f-butyl (6-bromo-1 ,3-benzothiazol-2-yl)carbamate (1.0 g; 3.04 mmol), 2-methoxypyridine-3-boronic acid (0.56 g; 3.65 mmol), PdCI2(PPh3)2 (0.1 1 g; 0.15 mmol) and cesium fluoride (1.38 g; 9.11 mmol) in dioxane (12 ml.) and water (6 ml.) was stirred at 900C for 3 h. The solution was diluted with DCM, washed successively with sat. aq. NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo. The residue was taken up in DCM and filtered through a short plug of alumina. After concentration in vacuo, the residue was triturated in MeOH and filtered to afford the title compound as a pale grey solid. 1H NMR (DMSO-d6, 300 MHz) δ 1 1.80 (s, 1 H),8.18 (dd, J = 1.8, 4.9 Hz, 1 H), 8.09 (d, J = 1.6 Hz, 1 H), 7.79 (dd, J = 1.8, 7.2 Hz, 1 H), 7.71 (d, J = 8.5, 1 H), 7.57 (dd, J = 1.8, 8.4 Hz, 1 H), 7.10 (dd, J = 4.9, 7.3 Hz, 1 H), 3.89 (s, 3H), 1.52 (s, 9H).

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2010/100144, 2010, A1 Location in patent: Page/Page column 157

10
[ 498-02-2 ]
[ 163105-90-6 ]
[ 943152-72-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 1-(3-methoxy-4-hydroxyphenyl)ethanone With N,N-phenylbistrifluoromethane-sulfonimide; potassium carbonate In tetrahydrofuran at 120℃; for 0.1h; Irradiation; Stage #2: 2-methoxypyridin-3-yl-boronic acid In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 120℃; for 0.166667h;	19 (R)-N-{1-[3-Methoxy-4-(2-methoxy-pyridin-3yl)-phenyl]-ethyl}-2-trifluoromethoxy-benzenesulfonamide A mixture of acetovanillone (0.332 g, 2.0 mmol), N-phenyl-bis(trifluoromethane-sulfonimide) (710 mg, 2.0 mmol), potassium carbonate (830 mg, 6.0 mmol) and tetrahydrofuran (3.0 ml) was heated to 120° C. for 6 min in a microwave oven. 2-Methoxypyridine-3-boronic acid (611 mg, 4 mmol), tetrakis(triphenylphosphine)palladium (0) (115 mg, 100 μmol), N-methylpyrrolidinone (1 ml) were then added and the mixture heated in the microwave at 120° C. for 10 min. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was separated and washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and the solvent evaporated to give 1-[3-methoxy-4-(2-methoxy-pyridin-3yl)-phenyl]-ethanone in quantitative yield. Reductive amination with ammonium acetate (20 equivalents) in methanol (50 ml) containing sodium cyanoborohydride (1 equivalent) followed by aqueous work-up with saturated aqueous sodium bicarbonate and extraction into ethyl actetate gave, after solvent was evaporated 1-[3-methoxy-4-(2-methoxy-pyridin-3yl)-phenyl]-ethylamine. To 1-[3-methoxy-4-(2-methoxy-pyridin-3yl)-phenyl]-ethylamine was added 2-trifluoromethoxy-benzenesulfonyl chloride (1 equivalent) in dichloromethane, diisopropylethylamine (4 equivalents) and the mixture overnight. The racemic product was isolated by normal phase HPLC on silica gel eluting with heptane/ethyl acetate and the solvent evaporated to give a clear oily solid (72 mg). 1H NMR (400 MHz, CDCl3): δ 8.15 (d, 1H), 7.9 (d, 1H), 7.5 (m, 1H), 7.4 (m, 1H), 7.3-7.2 (m, 2H), 7.05 (d, 1H), 6.9 (m, 1H), 6.75-6.65 (m, 2H), 5.0 (d, 1H), 4.55 (m, 1H), 3.91 (s, 3H), 3.67 (s, 3H), 1.51 (d, 3H) ppm; MS (ESI) m/z: 483.3 [M+1]+. The racemate was resolved by chiral HPLC (CHIRALPAK-AS, eluting with 9:1 isohexane/ethanol) to give the title compound (11 mg) and its enantiomer (11) mg.

Reference： [1]Current Patent Assignee: MERCK & CO INC; LIGAND PHARMACEUTICALS INC - US2007/149577, 2007, A1 Location in patent: Page/Page column 8-9

11
[ 13472-59-8 ]
[ 163105-90-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4479 - 4481

12
[ 870-50-8 ]
[ 163105-90-6 ]
[ 1338466-40-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper diacetate; In methanol; at 60℃; for 1h;	A mixture of 2-methoxypyridine-3-boronic acid (1.00 g, 6.54 mmol), di-tert-butyl azodicarboxylate (1.51 g, 6.54 mmol), copper(ii) acetate (39.2 mg, 0.216 mmol), and MeOH (10 mL) was heated to 60 C. and stirred for 1 h before cooling to room temperature. The mixture was concentrated under reduced pressure to give a yellow solid, which was solved in MTBE (100 mL) and washed with sat. aq. NaHCO3(100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford the title compound (2.2 g, 99%) as a yellow solid, which was used directly in the next step. LCMS (ESI) m/z M+1: 340.1.
	With copper(II) acetate monohydrate; In methanol; at 65℃; for 1h;	(2-methoxypyridin-3-yl)boronic acid (228 mg, 1.5 mmol), di-tert-butylazodicarboxylate ?DBAD? (230 mg, 1.0 mmol) and Cu(II)OAc-H2O (10 mg, 0.05 mmol) were combined in 6 mL MeOH in a 20 mL scintillation vial and heated for 1 h at 65 C. The mixture was cooled to room temperature and 4 mL 4N HCl in dioxane added stirred 15 mins then the mixture was concentrated to dryness under an air stream. To this residue was added cyclohexanone (150 mg, 1.5 mmol) and 2.8 mL 4% H2SO4(aq) and placed in a 1000C oil bath for 2 hrs then cooled to room temperature and volatiles were removed in vacuo to give a crude oil which was partitioned between 25 mL of sat. aq. NaHCO3 and 100 mL CH2Cl2 ans organics separated. Aqueous was extracted a second time with 75 mL CH2Cl2, combined, dried (MgSO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography though silica gel using ethyl acetate in heptanes to elute providing 124 mg (61%) of 1-methoxy-6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole (table 1, entry 1h) as a yellow solid.

Reference： [1]Patent: US2019/381019,2019,A1 .Location in patent: Paragraph 0586-0588
[2]Tetrahedron Letters,2012,vol. 53,p. 564 - 569

13
[ 2926-29-6 ]
[ 163105-90-6 ]
[ 121643-44-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4979 - 4981,3

14
[ 637-81-0 ]
[ 10134-91-5 ]
[ 85117-99-3 ]
[ 163105-90-6 ]
[ 1037763-25-9 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of freshly made sodium methoxide by dissolving (1.42 g, 62.0 mmol) of sodium in methanol (30 mL) was added dropwise to a solution of ethylazido acetate (7.99 g, 62 mmol), and 5.1 g (31 mmol) of aldehyde 5 in methanol (30 mL) at -20 C. The reaction mixture was slowly warmed to room temperature and stirred for 3 h. The reaction mixture was concentrated in vacuo and diluted with EtOAc. The organic layers were washed with water and dried (MgSO4), filtered, concentrated in vacuo and purified by chromatography using SiO2 (EtOAc/hexanes) to yield 6 (3 g) of yellow solid. It was further purified by crystallization using ether and hexanes to yield pure product (1.95 g).; A solution of azido ester 6 (1.9 g, 7.4 mmol) in xylenes was heated at reflux for 30 min, when the starting material completely disappears as indicated by TLC. On cooling the solution to room temperature and partial concentration of the xylenes, indole 7 (1.1 g) precipitated out of solution as a colorless solid.; A solution of indole 7 (1.00 g, 4.33 mmol) in DMF (20 mL) was treated with N-iodosuccinimide (1.07 g, 4.76 mmol) and stirred at rt for 12 h. The reaction mixture was concentrated in vacuo, diluted with water, and extracted in EtOAc (300 mL). The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and purified by chromatography (SiO2, EtOAc/hexanes) to yield iodinated compounds 8a and 8b as a colorless solid.; A solution of iodide (1.2 g, 3.35 mmol) in DME (25 mL) was treated with 2-methoxypyridin-3-ylboronic acid 9 (1.52 g, 10 mmol), Pd(dppf)Cl2·CH2Cl2 (324 mg) and stirred at rt under nitrogen for 0.25 h. The reaction mixture was treated with a solution of potassium carbonate (2.77 g, 20.1 mmol) in 25 mL of water and heated at 90 C. After 1 h, analysis of TLC of reaction mixture indicated complete consumption of starting material. The reaction mixture was diluted with EtOAc (300 mL), and washed with water. The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and purified by chromatography using EtOAc/hexanes (0 ? 70%) to yield 10a and 10b.; A solution of 10a and 10b (300 mg, 0.90 mmol) in DMF (10 mL) were treated with cesium carbonate (585 mg, 1.80 mmol), 2,5-difluorobenzyl bromide (372 mg, 1.80 mmol) and stirred at rt for 12 h. The reaction mixture was diluted with EtOAc (250 mL) and washed with brine (2 × 100 mL). The EtOAc layer was dried (MgSO4), filtered, concentrated in vacuo and purified by chromatography using SiO2 (EtOAc/hexanes) and once again with acetone/CH2Cl2 to yield N(1) alkylated products 10a and 10b as a colorless solid. The solid were taken in THF (20 mL) and water (20 mL), treated with lithium hydroxide and refluxed. The disappearance of starting material was followed by TLC. On complete consumption of starting material the mixture was diluted with EtOAc (200 mL) washed with water, brine and dried (MgSO4), filtered concentrated in vacuo to yield 12 that was used as is.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2007 - 2017

15
[ 76-09-5 ]
[ 163105-90-6 ]
[ 532391-31-4 ]

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

16
[ 3972-64-3 ]
[ 163105-90-6 ]
[ 1206770-85-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3115 - 3119

17
[ 3972-64-3 ]
[ 163105-90-6 ]
[ 1428941-79-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3115 - 3119

18
[ 211308-81-5 ]
[ 163105-90-6 ]
[ 1258627-32-5 ]

Yield	Reaction Conditions	Operation in experiment
21 g	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 24h;Inert atmosphere; Reflux;	2-methoxy-3-pyridylboronic acid (24.0 g, 157 mmol) and (40.0 g, 157 mmol) was dissolved in THF (900 ml), and oxygen in the solution was removed by nitrogen bubbling. Potassium carbonate (65.2 g, 472 mmol) was added to the solution, Distillation After dissolving in water (50 ml), oxygen was removed via nitrogen bubbling and added to the solution. To this was added tetrakistriphenylphosphino palladium(5.09 g, 4.72 mmol) And the mixture was stirred under reflux for 24 hours. The reaction solution was extracted with ethyl acetate, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 21.0 g of Intermediate 1. Intermediate 1 (21.0 g, 89.1 mmol) was dissolved in a mixed solvent of acetic acid / THF (200 ml / 100 ml) The temperature was lowered by -10 C. T-Butyl nitrite (27.6 g, 267 mmol) was slowly added and heated at the same temperature for 12 hours Lt; / RTI & gt; The reaction solution was extracted with distilled water and ethyl acetate, and then a mixed solvent of ethyl acetate / Rum chromatography was carried out to obtain 10.5 g of Intermediate 2.

Reference： [1]Chemical Communications,2013,vol. 49,p. 6185 - 6187
[2]Patent: KR101627026,2016,B1 .Location in patent: Paragraph 0139-0142

19
[ 446273-59-2 ]
[ 163105-90-6 ]
[ 1466574-56-0 ]

Yield	Reaction Conditions	Operation in experiment
49%		General procedure: To a solution of <strong>[446273-59-2]4-bromo-6-chloropyridazin-3-amine</strong> (2.5 g, 12.0 mmol, CAS RN 446273-59-2) in 1,2-dimethoxyethane (30 mL) was added 4-fluoro-2-methoxyphenylboronic acid (2.45 g, 14.4 mmol, CAS RN 179899-07-1) and 2M aqueous sodium carbonate solution (10 mL). The reaction mixture was stirred under argon atmosphere for 15 minutes. Pd(II)acetate (135 mg, 600 mumol) and triphenylphosphine (315 mg, 1.2 mmol) was added. The dark red reaction mixture was stirred at 90 C. for 8 hours and then poured on 10% aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL), filtered over dicalite and the layers were separated. The aqueous layer was extracted a second time with ethyl acetate (200 mL). The organic layers were washed with 200 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography on a 120 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Light red solid (1.71 g, 56.2%). MS (ESI+): m/z=254.050 ([M+H]+). The title compound was prepared in analogy to example 1, intermediate b, from 4-bromo-6-chloropyridazin- 3-amine (CAS RN 446273-59-2) and 2-methoxypyridine-3- boronic acid (CAS RN 163105-90-6) after a reaction time of 18 hours. Brown solid (49%). MS (ESIj: mlz=237.054 ([M+ H]).

Reference： [1]Patent: US2013/267519,2013,A1 .Location in patent: Paragraph 0220; 0244

20
[ 50-00-0 ]
[ 163105-90-6 ]
[ 112197-16-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis(eta3-allyl-mu-chloropalladium(II)); 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-4,5-dihydroimidazolinium chloride; In tetrahydrofuran; water; at 100℃; for 2h;Inert atmosphere; Sealed tube;	General procedure: [PdCl(eta3-allyl)]2 (0.00125-0.005 mmol), imidazolinium salt 1a (0.0025-0.01 mmol), arylboronic acid (0.50 mmol) and an inorganic base (2.0 mmol) were charged in a 10 mL test tube sealed with a rubber septum. The test tube was evacuated and backfilled with argon. This sequence was repeated five times. Then solvent (0.5 mL) and 37 wt % formaldehyde in H2O (102 mg, formaldehyde 1.25 mmol) were added via the rubber septum with syringe. In anargon flow, the rubber septum was replaced with a Teflon liners crew cap. The test tube was placed in an oil bath preheated at 100 C. The reaction mixture was stirred for 2 h and was cooled to room temperature. Then, operation of (i) or (ii) was performed. (i)The obtained crude was purified by passing it through a silica gel column with a hexane/ethyl acetate eluent (Table 4 entry 2 and Table 5 entries 8-16). (ii) Diphenylmethane (84.1 mg, 0.50 mmol) as an internal standard was added and then an aliquot of the organic layer of the reaction mixture was subjected to the quantitative analysis by 1H NMR (Table 4).

Reference： [1]Tetrahedron,2014,vol. 71,p. 19 - 26

21
[ 42330-59-6 ]
[ 163105-90-6 ]
[ 7631-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	GBT925-6-((2'-methoxy-[2,3'-bipyridin]-3-yl)methoxy)-1H-indazole-7-carbaldehyde The compound was prepared from <strong>[42330-59-6](2-chloropyridin-3-yl)methanol</strong> and (2-methoxypyridin-3-yl)boronic acid according to scheme 1, reaction steps 1, 2 and 4. In step 4, alkylation with 6-hydroxy-1H-indazole-7-carbaldehyde with 3-(chloromethyl)-2'-methoxy-2,3'-bipyridine HCl salt, the product as white solid was obtained after SiO2 column purification. 1H NMR (400 MHz, CDCl3) delta 11.53 (s, 1H), 10.46 (s, 1H), 8.69 (dd, J=1.67, 4.81 Hz, 1H), 8.26 (dd, J=1.95, 5.01 Hz, 1H), 7.98 (d, J=0.99 Hz, 1H), 7.94 (dd, J=0.82, 6.99 Hz, 1H), 7.85 (d, J=8.86 Hz, 1H), 7.73 (dd, J=1.95, 7.27 Hz, 1H), 7.05 (dd, J=5.03, 7.28 Hz, 1H), 6.68 (d, J=8.89 Hz, 1H), 5.22 (s, 1H), 3.94 (s, 3H). MS (ESI) m/z 361 [M+H]+.

Reference： [1]Patent: US2015/259296,2015,A1

22
[ 75-05-8 ]
[ 163105-90-6 ]
[ 7254-34-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With N-iodo-succinimide; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,1,2,2,2-hexamethyldisilane; oxygen; copper diacetate; diisopropylamine at 20 - 150℃; Schlenk technique;

Reference： [1]Zhu, Yamin; Li, Linyi; Shen, Zengming [Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13246 - 13252]

23
[ 163105-90-6 ]
[ 13472-83-8 ]

Reference： [1]Chemical Science,2017,vol. 8,p. 1551 - 1559

24
[ 762-51-6 ]
[ 163105-90-6 ]
3-(2-fluoroethyl)-2-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium phosphate; 4,4'-Dimethoxy-2,2'-bipyridin; nickel dibromide; In diethylene glycol dimethyl ether; at 80℃; for 20h;Inert atmosphere; Sealed tube;	In a nitrogen atmosphere, 2-methoxypyridine-3-boronic acid (2.294 g, 15.0 mmol) was added sequentially to the tube.Anhydrous potassium phosphate (6.368g, 30.0mmol),Add solvent diethylene glycol dimethyl etherAfter stirring (60mL),Then add <strong>[762-51-6]1-fluoro-2-iodoethane</strong> in turn(1.739g, 10.0mmol),4,4'-dimethoxy-2,2'-dipyridyl(0.238 g, 1.1 mmol)And NiBr2 (0.219 g, 1.0 mmol),After sealing, the reaction is stirred for 20 hours in an oil bath at 80C.Cool the reaction solution to room temperatureThe insoluble matter in the reaction solution was filtered off with a celite sand core funnel.A small amount of ether was rinsed and the filtrate was collected.To the filtrate was added 60 mL of water,The aqueous phase was extracted with ether (40 mL×3).The organic phase is combined and the organic phase isIt is washed with saturated saline, dried over anhydrous sodium sulfate and filtered.Rotary evaporation recovers solventThe residue was subjected to silica gel column chromatography to give 1.195 g of a product in a 77% yield.

Reference： [1]Patent: CN107628926,2018,A .Location in patent: Paragraph 0198-0202
[2]Chemical Science,2019,vol. 10,p. 5275 - 5282

25
[ 163105-90-6 ]
[ 112197-15-6 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 2488 - 2492

26
[ 3993-78-0 ]
[ 163105-90-6 ]
[ 1035944-51-4 ]

Yield	Reaction Conditions	Operation in experiment
61%		A 100 mL round bottom flask wassequentially charged with Pd(OAc)2 (0.12 g, 2 %mol), PtBu3HBF4 (0.18 g, 2.4 %mol),<strong>[3993-78-0]2-Amino-4-chloropyrimidine</strong> (4 g), 2-methoxy-3-pyridinylboronic acid (5.65 g, 1.2 eq.), and 40 mL ofn-butanol. Mixture was stirred at 80 C under nitrogen for 15 min and then NaOH (2.09 g, 1.7 eq.)was added to initiate the reaction. After 30 min, the heating was stopped and the reaction was stirredovernight. After 15 h, the reaction mixture was poured over 300 mL Et2O, the precipitate separated,and the organic phase was concentrated on rotary evaporator. Afterwards, resulting residue wasrecrystalized twice from MeOH giving 4.07 g of white-yellow crystals (61% yield). M.p. 151-154 C(dec.). 1H NMR (TMS, DMSO, 400.13 MHz, 295 K) : 8.30-8.28 (m, 3H), 7.18-7.14 (m, 2H), 6,67 (bs,2H), and 3.96 (s, 3H). 13C NMR (TMS, DMSO, 100.61 MHz, 295 K) : 164.14, 161.43, 161,27, 158.97,148.61, 139.43, 120.96, 117.81, 110.38, and 53.96. Elemental for C, 59.40; H, 4.98; N, 27.71; found C, 59.46;H, 5.08; N, 27.65.

Reference： [1]Molecules,2019,vol. 24

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[ CAS No. 163105-90-6 ] {[proInfo.proName]}

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[ 163105-90-6 ] Synthesis Path-Upstream 1~7

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Organoboron

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Pyridines

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