[ CAS No. 1171891-42-1 ] {[proInfo.proName]}

Name: 1171891-42-1|3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|97%
Brand: Ambeed
SKU: A109941
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Quality Control of [ 1171891-42-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1171891-42-1 ]

Product Details of [ 1171891-42-1 ]

CAS No. :	1171891-42-1	MDL No. :	MFCD09265531
Formula :	C₁₂H₁₈BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SYEVQHAWWSEMRN-UHFFFAOYSA-N
M.W :	219.09	Pubchem ID :	17750283
Synonyms :

Calculated chemistry of [ 1171891-42-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.58
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	65.68
TPSA :	31.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.2
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	0.86
Log Po/w (SILICOS-IT) :	1.79
Consensus Log Po/w :	1.31

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.8
Solubility :	0.351 mg/ml ; 0.0016 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.705 mg/ml ; 0.00322 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.02
Solubility :	0.021 mg/ml ; 0.0000959 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.89

Safety of [ 1171891-42-1 ]

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

Application In Synthesis of [ 1171891-42-1 ]

* 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 [ 1171891-42-1 ]

[ 1171891-42-1 ] Synthesis Path-Downstream 1~19

1
3-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine [ No CAS ]
[ 3430-16-8 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 15434 - 15435

2
5-methylpyridin-3-ylboronic acid pinacol ester [ No CAS ]
[ 19230-55-8 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 15434 - 15435

3
[ 108-99-6 ]
[ 73183-34-3 ]
[ 1171891-42-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	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: 3-Methylpyridine In para-xylene at 80℃; for 9h; Schlenk technique; regioselective reaction;
	In tetrahydrofuran at 80℃; for 16h;
	With C₄₄H₇₂B₃IrN₂O₆ In tetrahydrofuran at 65℃; Inert atmosphere;

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]Murphy, Jaclyn M.; Liao, Xuebin; Hartwig, John F. [Journal of the American Chemical Society, 2007, vol. 129, # 50, p. 15434 - 15435]
[3]Larsen, Matthew A.; Hartwig, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299]

5
[ 1171891-42-1 ]
[ 1362850-84-7 ]
[ 343338-28-3 ]
[ 1362850-91-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine; 2-methylpropane-2(S)-sulfinic acid N-(2,8-dichloroquinolin-3-yl)meth-(E)-ylideneamide With sodium hydrogencarbonate In 1,4-dioxane; water for 2h; Inert atmosphere; Reflux; Stage #2: (S)-2-methylpropane-2-sulfinamide With potassium phosphate In water; isopropyl alcohol at 60℃;	16 INTERMEDIATE 162-Methylpropane-2(6 -sulfinic acid N-[8-chloro-2-(5-methylpyridin-3-yl)quinolin-3-yll- meth-(E)-ylideneamideA mixture of Intermediate 9 (2.0 g, 6.08 mmol), 5-methylpyridin-3-ylboronic acid pinacol ester (1.6 g, 7.31 mmol), tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.31 mmol) and 2M aqueous sodium bicarbonate solution (5 mL) in 1,4-dioxane (25 mL) was degassed and heated under reflux in a nitrogen atmosphere for 2 h. The reaction mixture was cooled to room temperature, partitioned between DCM and brine, and the aqueous layer was extracted once more using EtOAc. The combined organic extracts were dried (MgS04) and the solvent was removed under reduced pressure. To a solution of the resulting material in 2-propanol (10 mL) was added a solution prepared by stirring potassium phosphate (1.2 g, 5.66 mmol) and (5)-2-methyl-2-propanesulfinamide (0.75 g, 6.2 mmol) in water (10 mL) for 15 minutes. The reaction mixture was stirred overnight, then incubated at 60°C for a further 24 h. DCM was added and washed with brine, the organic extract was dried (MgS04) and the solvent was removed in in vacuo. Column chromatography (Si02, 50-60% EtOAc in hexane) gave the title compound (2.28 g, 97%) as a pale yellow foam. δΗ (CDC13) 8.93 (s, 1H), 8.81 (s, 1H), 8.63 (m, 1H), 7.98 (m, 2H), 7.69 (m, 1H), 7.61 (m, 1H), 7.50 (m, 1H), 2.54 (s, 3H), 1.31 (s, 9H). LCMS (ES+) 386 (M+H)+, RT 1.56 minutes.

Reference： [1]Current Patent Assignee: UCB - WO2012/32334, 2012, A1 Location in patent: Page/Page column 31

6
[ 1171891-42-1 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran-d8 at 30℃; Inert atmosphere; Glovebox;

Reference： [1]Larsen, Matthew A.; Hartwig, John F. [Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299]

7
[ 1171891-42-1 ]
[ 1447607-95-5 ]
[ 1428521-53-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃;

Reference： [1]Whitehead, Brent R.; Lo, Michael M.-C.; Ali, Amjad; Park, Min K.; Hoyt, Scott B.; Xiong, Yusheng; Cai, Jiaqiang; Carswell, Emma; Cooke, Andrew; MacLean, John; Ratcliffe, Paul; Robinson, John; Bennett, D. Jonathan; Clemas, Joseph A.; Wisniewski, Tom; Struthers, Mary; Cully, Doris; MacNeil, Douglas J. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 143 - 146]

8
[ 945400-80-6 ]
[ 1171891-42-1 ]
[ 2445548-80-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 2-bromanyl-1,3-benzothiazol-6-amine; 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water	110.110-1 Step 1-1: Preparation of 4-(pyrimidin-2-yl)aniline General procedure: 2-bromopyrimidine under nitrogen(175 mg, 1.10 mmol)And 4-aminophenylboronic acid pinacol ester(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 200 mg, 0.91 mmol)Was dissolved in 15 mL of 1,4-dioxane solution,Pd(PPh3)2Cl2 (63 mg, 0.09 mmol)And 1.0 M aqueous sodium carbonate solution (3.64 mL, 3.64 mmol) were added.The reaction mixture was stirred at 80° C. for 12 hours.When the reaction was completed, extraction was performed using distilled water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the concentrate was purified by column chromatography to give 115 mg (yield 74%) of the title compound.
45%	Stage #1: 2-bromanyl-1,3-benzothiazol-6-amine; 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane	110.110-1 Step 1-1: Preparation of 4-(pyrimidin-2-yl)aniline General procedure: 2-Bromopyrimidine (175 mg, 1.10 mmol) and 4-aminophenylboronic acid pinacol ester (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline) (200 mg, 0.91 mmol) were dissolved in 15 mL of a 1,4-dioxane solution in the presence of nitrogen, and then Pd(PPh3)2Cl2 (63 mg, 0.09 mmol) and a 1.0 M aqueous sodium carbonate solution (3.64 mL, 3.64 mmol) were added to obtain a reaction mixture. The reaction mixture was stirred at 80°C for 12 hours. When the reaction was completed, the reaction product was extracted using distilled water and ethyl acetate to obtain an organic layer, and the organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the concentrate was purified by column chromatography to obtain 115 mg (74% yield) of the title compound.

Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - KR2020/76655, 2020, A Location in patent: Paragraph 0325; 0327; 0328; 1414; 1501; 1503-1505
[2]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - EP3901139, 2021, A1 Location in patent: Paragraph 0069; 0300; 0302; 0320

9
[ 1171891-42-1 ]
[ 1073525-72-0 ]
[ 2369012-52-0 ]

Yield	Reaction Conditions	Operation in experiment
560 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In ethanol; water; toluene at 120℃; for 4h; Inert atmosphere;	5.2 5. Synthesis of Compound 211 (1) Compound (1.0 g, 5.8 mmol, 1.0 eq), bis-boronic acid pinacol ester (1.6 g, 6.38 mmol, 1.1 eq),and potassium acetate (1.1 g, 11.6 mmol, 2.0 eq) were placed in a 100 mL round bottom flask, added with toluene (40 mL) and then subjected to replacement of nitrogen gas once, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (237 mg, 0.29 mmol, 0.05 eq), and then subjected to replacement of nitrogen gas three times, and then heated to 120°C and reacted for 16 h. The system was cooled to room temperature, and Compound II (1.48g, 5.8mmol, 1.0eq), K2CO3 (1.6g, 11.6mmol, 2.0eq), 95% ethanol (8mL) and Pd(dppf)Cl2CH2Cl2 (237mg, 0.29mmol, 0.05eq) were added, and then subjected to replacement of nitrogen gas three times, and heated to 120°C (reflux) and reacted for 4h. After the reaction was complete detected by LCMS, the reaction mixture was concentrated and then added with silica gel and purified by column chromatography to give obtain Compound 211-b (560mg, Y: 36%).

Reference： [1]Current Patent Assignee: QINGDAO KING AGROOT PLANT PROTECTION SERVICE CO LTD - EP3747870, 2020, A1 Location in patent: Paragraph 0094

10
[ 3430-16-8 ]
[ 73183-34-3 ]
[ 1171891-42-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; XPhos In 1,4-dioxane for 20h; Schlenk technique; Inert atmosphere; Heating;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In toluene at 120℃; for 16h; Inert atmosphere;	5.1 5. Synthesis of Compound 211 (1) Compound (1.0 g, 5.8 mmol, 1.0 eq), bis-boronic acid pinacol ester (1.6 g, 6.38 mmol, 1.1 eq),and potassium acetate (1.1 g, 11.6 mmol, 2.0 eq) were placed in a 100 mL round bottom flask, added with toluene (40 mL) and then subjected to replacement of nitrogen gas once, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (237 mg, 0.29 mmol, 0.05 eq), and then subjected to replacement of nitrogen gas three times, and then heated to 120°C and reacted for 16 h. The system was cooled to room temperature, and Compound II (1.48g, 5.8mmol, 1.0eq), K2CO3 (1.6g, 11.6mmol, 2.0eq), 95% ethanol (8mL) and Pd(dppf)Cl2CH2Cl2 (237mg, 0.29mmol, 0.05eq) were added, and then subjected to replacement of nitrogen gas three times, and heated to 120°C (reflux) and reacted for 4h. After the reaction was complete detected by LCMS, the reaction mixture was concentrated and then added with silica gel and purified by column chromatography to give obtain Compound 211-b (560mg, Y: 36%).

Reference： [1]Trobe, Melanie; Schreiner, Till; Vareka, Martin; Grimm, Sebastian; Wölfl, Bernhard; Breinbauer, Rolf [European Journal of Organic Chemistry, 2022, vol. 2022, # 17]
[2]Current Patent Assignee: QINGDAO KING AGROOT PLANT PROTECTION SERVICE CO LTD - EP3747870, 2020, A1 Location in patent: Paragraph 0094

11
[ 1171891-42-1 ]
[ 2369003-96-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; toluene; ethanol / 4 h / 120 °C / Inert atmosphere 2: potassium acetate / dimethyl sulfoxide / 3 h / 125 °C

Reference： [1]Current Patent Assignee: QINGDAO KING AGROOT PLANT PROTECTION SERVICE CO LTD - EP3747870, 2020, A1

12
[ 1171891-42-1 ]
[ 2368820-73-7 ]
[ 2368820-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 100℃; for 3h;	13.1 Step 1: synthesis of compound 0023 General procedure: Compound BB-3-1 (100 mg, 268.66 µmol, 1 eq) is added to dioxane (2.0 mL) and water (1.0 mL), and then compound BB-1 (72 mg, 268.66 µmol, 1 eq), tetratriphenylphosphine palladium (31 mg, 26.87 µmol, 0.1 eq) and potassium carbonate (111 mg, 805.97 µmol, 3 eq) are added. The reaction solution is reacted at 100°C for 3 hours. The reaction solution is added with ethyl acetate (50.0 mL), washed with saturated brine (20.0 mL) once, dried over anhydrous sodium sulfate and filtered, and the filtrate is concentrated to obtain a crude black solid. The crude product is separated and purified by high-performance liquid chromatography (column: YMC-Actus Triart C18 100 FontWeight="Bold" FontSize="10" 30 mm FontWeight="Bold" FontSize="10" 5 µm; mobile phase: [water (0.05%HCl)-ACN]; B%: 40%-70%, 10 minutes) to obtain the hydrochloride salt of compound 0023. The salt is dissolved in ethyl acetate, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate and filtered, and the filtrate is concentrated to obtain compound 0023. Hydrochloride salt of compound 0023: MS (ESI) m/z: 433.8 [M+H]+. 1H NMR (400 MHz, MeOH) δ: 8.88 (s, 1 H) 8.29 (s, 1 H) 7.98 (s, 1 H) 7.39 (s, 2 H) 6.67 (s, 1 H) 3.95 (s, 3 H) 3.87 (s, 6H) 3.83 (s, 3 H), 2.57 (s, 3 H).

Reference： [1]Current Patent Assignee: ZHANGZHOU PIENTZEHUANG PHARMACEUTICAL CO., LTD. - EP3750880, 2020, A1 Location in patent: Paragraph 0102; 0103; 0129; 0130

13
[ 1171891-42-1 ]
[ 2640544-00-7 ]
[ 2640642-08-4 ]

Yield	Reaction Conditions	Operation in experiment
54 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.416667h; Inert atmosphere;	55.1 Step 1: To a mixture of building block BB6 (150 mg, 498 umol, 1.0 eq) and 3-methyl-5-(4, 4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (130 mg, 598 umol, 1.2 eq) in dioxane (2.1 mL) and H20 (0.1 mL) was added CS2CO3 (325 mg, 996 umol, 2 eq) and Pd(dppf)Cl2.CH2Cl2 (81 mg, 99 umol, 0.2 eq) in one portion at 25°C under N2. The mixture was degassed and recharged with nitrogen, repeated three times. The mixture was heated and stirred at 120°C for 25 minutes. TLC (Petroleum ether : Ethyl acetate = 1:1) showed the starting material was consumed completely and one major new spot was detected. After cooling, the mixture was filtered, and the filter cake was washed with ethyl acetate (10 mL x 2). The combined filtrates were washed with brine (10 mL), dried over Na2SC>4, filtered and concentrated under reduced pressure to dryness. The residue was purified by prep- TLC (S1O2, Ethyl acetate : MeOH = 10:1) to give 55a (54 mg, 34.6%) as yellow oil.

Reference： [1]Current Patent Assignee: AMBYS MEDICINES - WO2021/76945, 2021, A1 Location in patent: Page/Page column 104

14
[ 1171891-42-1 ]
[ 2410554-15-1 ]
[ 2410554-08-2 ]

Yield	Reaction Conditions	Operation in experiment
1.4%	With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h;	5 Preparation of the compound THK-5474 To a solution of the compound 3 (prepared according to the process described in Preparation example 1) (159.7 mg, 0.62 mmol), and the compound 8 (163 mg, 0.74 mmol) in 1,2-dimethoxyethane (1.7 mL) were added sodium carbonate (178 mg, 1.68 mmol), water (0.75 ml), bis(triphenylphosphine)palladium (II) dichloride (4.3 mg, 0.006 mmol), and the mixture was heated at 90°C under reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, and thereto was added water, and the mixture was extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and the filtrates were evaporated under reduced pressure. The residue was purified by flash chromatography (eluting solvent: ethyl acetate: methanol = 100/0 → 90/10) to obtain the compound THK-5474 as white solid (7.7 mg, 0.025 mmol, 1.4 %). 1H-NMR (600 MHz, CDCl3) δ 9.10 (s, 1H), 8.52 (s, 1H), 8.32 (s, 1H), 8.15 (d, J = 8.5 Hz, 1H), 8.09 (d, J = 9.2 Hz, 1H), 7.85 (d, J = 8.5 Hz, 1H), 7.43-7.41 (m, 1H), 7.15 (m, 1H), 4.73-4.68 (m, 1H), 4.65-4.60 (m, 1H), 4.37-4.34 (m, 1H), 4.26-4.22 (m, 1H), 2.47 (s, 3H). MALDI MS m/z = 313 [M+H]+

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - EP3835293, 2021, A1 Location in patent: Paragraph 0132; 0177-0178

15
[ 1171891-42-1 ]
[ 2659367-70-9 ]
[ 2659366-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); sodium carbonate In 1,4-dioxane; water at 100℃;	228 Example 227.8-chloro-N-(3-(5-cyclopropylpyridin-3-yl)phenyl)-N-methyl- [1,2,4]triazolo[4,3-a]quinazolin-5-amine General procedure: A vigorously stirred mixture of Example 308 (9.5 mg, 24.4 µmol), (5-cyclopropyl-3- pyridyl)boronic acid (6.05 mg, 37.1 μmol), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.73 mg, 2.4 µmol), and aqueous sodium carbonate solution (2.0 M, 122 μL, 244 μmol) in 1,4-dioxane (0.5 mL) was heated to 100 °C. After 5 min, the resulting mixture was cooled to room temperature and was concentrated under reduced pressure. The residue was purified by reverse-phase preparative HPLC (0.1% trifluoroacetic acid in acetonitrile/water) to give the title compound: 1H NMR (400 MHz, Acetone-d6) δ 9.48 (s, 1H), 8.63 (s, 1H), 8.53 - 8.24 (m, 2H), 7.80 (t, J = 2.1 Hz, 1H), 7.68 (q, J = 4.0, 2.2 Hz, 2H), 7.59 (t, J = 7.8 Hz, 1H), 7.48 (dd, J = 22.1, 8.2 Hz, 2H), 7.36 - 7.23 (m, 1H), 3.72 (s, 3H), 1.17 - 1.00 (m, 2H), 0.83 (dt, J = 6.6, 4.3 Hz, 2H); LCMS(m/z) 427.3.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC; CARNA BIOSCIENCES, INC. - WO2021/130638, 2021, A1 Location in patent: Paragraph 1491-1492

16
[ 1171891-42-1 ]
[ 1825313-79-8 ]
[ 2770448-27-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In N,N-dimethyl-formamide at 80℃; Schlenk technique; Inert atmosphere;

Reference： [1]Trobe, Melanie; Schreiner, Till; Vareka, Martin; Grimm, Sebastian; Wölfl, Bernhard; Breinbauer, Rolf [European Journal of Organic Chemistry, 2022, vol. 2022, # 17]

17
[ 1171891-42-1 ]
[ 2770448-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / N,N-dimethyl-formamide / 80 °C / Schlenk technique; Inert atmosphere 2: caesium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / N,N-dimethyl-formamide / 80 °C / Schlenk technique; Inert atmosphere

Reference： [1]Trobe, Melanie; Schreiner, Till; Vareka, Martin; Grimm, Sebastian; Wölfl, Bernhard; Breinbauer, Rolf [European Journal of Organic Chemistry, 2022, vol. 2022, # 17]

18
[ 1171891-42-1 ]
[ 2770448-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / N,N-dimethyl-formamide / 80 °C / Schlenk technique; Inert atmosphere 2: caesium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / N,N-dimethyl-formamide / 80 °C / Schlenk technique; Inert atmosphere 3: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

Reference： [1]Trobe, Melanie; Schreiner, Till; Vareka, Martin; Grimm, Sebastian; Wölfl, Bernhard; Breinbauer, Rolf [European Journal of Organic Chemistry, 2022, vol. 2022, # 17]

19
[ 1171891-42-1 ]
[ 2798063-90-6 ]
[ 2798063-91-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 90℃; Inert atmosphere;	14.S7 S7: Synthesis of (3aS, 4S, 6R, 6aR)-6-(6-(benzylamino)-2-(pyridin-3-yl)-9H-purin-9-yl)-N-methyl-D3,2 ,2-dimethyl-tetrahydrofuran[3,4-d][1,3]dioxin-4-carboxamide General procedure: (3aS,4S,6R,6aR)-6-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-N-methyl-D3,2,2-dimethyl- Tetrahydrofuran[3,4-d][1,3]dioxy-4-carboxamide (200 mg, 0.4 mmol) was dissolved in a mixed solvent of tetrahydrofuran (10 mL) and water (5 mL), potassium carbonate (180 mg, 1.3 mmol), pyridin-3-ylboronic acid (136 mg, 0.9 mmol) and Pd(PPh3)4 (50 mg, 0.04 mmol). Under nitrogen protection, the temperature was raised to 120° C. and stirred at high pressure overnight, and the reaction was completed by TLC detection. Water was added to quench the reaction, extracted with ethyl acetate, the organic layers were combined, the organic layers were washed with water and saturated brine, the organic layers were collected, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=2:1) to obtain the title compound as a white solid (90 mg, 42% yield).

Reference： [1]Current Patent Assignee: ZHEJIANG VIMGREEN PHARMACEUTICALS - WO2022/143740, 2022, A1 Location in patent: Page/Page column 122; 124; 212; 214

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[ 1171891-42-1 ]

Organoboron

[ 1012085-50-5 ]

3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.89

[ 610768-32-6 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.89

[ 879291-27-7 ]

2-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.87

[ 893567-09-4 ]

2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.87

[ 1054483-78-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol

Similarity: 0.87

Related Parent Nucleus of
[ 1171891-42-1 ]

Pyridines

[ 1012085-50-5 ]

3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.89

[ 610768-32-6 ]

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.89

[ 879291-27-7 ]

2-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.87

[ 893567-09-4 ]

2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.87

[ 1054483-78-1 ]

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol

Similarity: 0.87

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1171891-42-1 ] {[proInfo.proName]}

Quality Control of [ 1171891-42-1 ]

Related Doc. of [ 1171891-42-1 ]

Product Details of [ 1171891-42-1 ]

Calculated chemistry of [ 1171891-42-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1171891-42-1 ]

Application In Synthesis of [ 1171891-42-1 ]

[ 1171891-42-1 ] Synthesis Path-Downstream 1~19

Related Functional Groups of [ 1171891-42-1 ]

Organoboron

Related Parent Nucleus of [ 1171891-42-1 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1171891-42-1 ]

Related Parent Nucleus of
[ 1171891-42-1 ]