[ CAS No. 108281-79-4 ] {[proInfo.proName]}

Name: 108281-79-4|6-Bromo-[1,2,4]triazolo[4,3-a]pyridine|97%
Brand: Ambeed
SKU: A104857
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Quality Control of [ 108281-79-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 108281-79-4 ]

CAS No. :	108281-79-4	MDL No. :	MFCD08689506
Formula :	C₆H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PFKZKSHKBBUZKU-UHFFFAOYSA-N
M.W :	198.02	Pubchem ID :	17750018
Synonyms :

Calculated chemistry of [ 108281-79-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.69
TPSA :	30.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.55
Log Po/w (XLOGP3) :	1.87
Log Po/w (WLOGP) :	1.49
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	1.2
Consensus Log Po/w :	1.52

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.243 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (Ali) :	-2.13
Solubility :	1.48 mg/ml ; 0.00749 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.57
Solubility :	0.533 mg/ml ; 0.00269 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.7

Safety of [ 108281-79-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 108281-79-4 ]

* 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 [ 108281-79-4 ]
Downstream synthetic route of [ 108281-79-4 ]

[ 108281-79-4 ] Synthesis Path-Upstream 1~3

1
[ 77992-44-0 ]
[ 122-51-0 ]
[ 108281-79-4 ]

Yield	Reaction Conditions	Operation in experiment
79.77%	at 110℃; for 20 h;	To a mixture of 5-bromo-2-hydrazinylpyridine (7.87 g, 42 mmol) in 200 mL of diethoxymethoxyethane was added p-toluenesulfonic acid (0.30 g, 1.7 mmol), and the mixture was heated to 110° C. and stirred further for 20 hours, then cooled to rt, and concentrated in vacuo. The residue was diluted with H₂O (150 mL). The resulted mixture was washed with aqueous NaHCO₃ solution (saturated, 40 mL), and extracted with DCM (300 mL*3). The combined organic phases were dried over anhydrous Na₂SO₄, and concentrated in vacuo. The residue was purified by a flash silica gel chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as a yellow solid (6.60 g, 79.77percent). MS (ESI, pos. ion) m/z: 197.9 [M+H]⁺; ¹H NMR (600 MHz, CDCl₃): δ 8.82 (s, 1H), 8.34 (s, 1H), 7.75 (d, J=9.7 Hz, 1H), 7.36 (d, J=9.7 Hz, 1H).

Reference： [1] Patent: US2014/134133, 2014, A1, . Location in patent: Paragraph 0451

2
[ 624-28-2 ]
[ 108281-79-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 4, p. 1071 - 1077
[2] Patent: US2014/134133, 2014, A1,

3
[ 14036-06-7 ]
[ 77992-44-0 ]
[ 108281-79-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 4, p. 1071 - 1077

[ 108281-79-4 ] Synthesis Path-Downstream 1~30

1
[ 14036-06-7 ]
[ 77992-44-0 ]
[ 108281-79-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1071 - 1077

2
[ 705293-00-1 ]
[ 108281-79-4 ]
[2-dimethylcarbamoyl-1-(3-fluoro-pyrrolidine-1-carbonyl)-2-(4-[1,2,4]triazolo[4,3-a]pyridin-6-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627

3
[ 108281-79-4 ]
3-amino-4-(3-fluoro-pyrrolidin-1-yl)-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[4,3-a]pyridin-6-yl-phenyl)-butyramide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3614 - 3627

4
[ 624-28-2 ]
[ 108281-79-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1071 - 1077
[2]Patent: US2014/134133,2014,A1

5
[ 1084812-43-0 ]
[ 108281-79-4 ]
[ 1084810-52-5 ]

Yield	Reaction Conditions	Operation in experiment
20%		To mixture of the boronate ester (0.3 g, crude) from step A above, 6-bromo-[l,2,4]triazolo[4,3-alpha]pyridine (0.32 g, 1.64 mmol), and cesium carbonate (0.80 g, 2.47 mmol) in a solution of DMF (5 mL) and water (1.25 mL) was <n="103"/>purged with argon for about 10 minutes. 1,1'-Bis(diphenylphosphino)ferrocenedichloropalladium (40 mg, 0.05 mmol) was added to the mixture, which was then heated at 80 0C for 4 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue obtained was purified by by reverse phase semi-preparative HPLC (5% B to 50% B over 50 min; A = 95:5 water/acetonitrile + 0.05% TFA, B = 95:5 acetonitrile/water + 0.05% TFA), and converted into the corresponding free base using 2N sodium carbonate to give the coupled product (70 mg, 20%) as a brown foam, which was resolved by preparative chiral HPLC (CHIRALPAK AD column, using 80:20:0.1 heptanes/isopropanol/diethylamine as the eluent) to give enantiomer A and enantiomer B. Enantiomer A was subjected to flash column chromatography (dichloromethane, then 95:4.5:0.5 to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide) to remove traces of diethylamine. Enantiomer B was subjected to further chiral purification (CHIRALCEL OD column, using 80:20:0.1 heptanes/ethanol/diethylamine as the eluent), followed by flash column chromatography (dichloromethane, then 95:4.5:0.5 to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide).

Reference： [1]Patent: WO2008/141082,2008,A1 .Location in patent: Page/Page column 101-102

6
[ 1160789-94-5 ]
[ 108281-79-4 ]
[ 1160789-95-6 ]

Yield	Reaction Conditions	Operation in experiment
2%		A solution of 6-bromo-[1 ,2,4]triazolo[4,3-a]pyridine (0.080 g, 0.40 mmol), 1 -ethyl-3-(5- (4,4,5, 5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzo [d]thiazol-2-yl)urea III (0.21 g, <n="24"/>0.60 mmol) and K3PO4 (0.13 g, 0.60 mmol) in DMF-H2O (7.0 mL, 2:1) was degassed by flushing with nitrogen for 15 min. Dichlorobis(triphenylphosphine)-palladium(ll) (0.04 g, 0.05 mmol) was then added to the reaction mixture followed by degassing with nitrogen for another 15 min. The resulting reaction mixture was then heated to 8O0C for 16 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to room temperature and poured onto ice-cold water followed by extraction with EtOAc (2 x 50 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was then purified over silica gel (230-400 M, 3.50% MeOH-DCM) to obtain the desired product (0.003 g, 2%). 1H-NMR (400 MHz, DMSO-Cl6): delta 1.11 (t, J= 7.20 Hz, 3H), 3.19 (m, 2H), 6.72 (br s, 1H), 7.55 (dd, J= 1.60 and 8.40 Hz, 1H), 7.80-7.96 (m, 3H), 8.02 (d, J= 8.0 Hz, 1 H), 8.97 (s, 1H), 9.25 (s, 1 H) and 10.82 (br s, 1 H). MS: 339.24 (M+H)+. Qualitative HPLC Purity (Acquity BEH C-18, 100 x 2.1 mm, 255 nm): 99.03% (Rt = 4.63 min).

Reference： [1]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 22-23

7
[ 108281-79-4 ]
[ 139301-27-2 ]
[ 1262618-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 150℃; for 0.5h;Inert atmosphere; microwave irradiation;	In a 5 mL vial <strong>[108281-79-4]6-bromo-[1,2,4]triazolo[4,3-a]pyridine</strong> (93 mg), 4-trifluoromethoxyphenylboronie acid (115 mg), and potassium carbonate (187 mg) were suspended in DMF (2 mL) that was previously degassed with nitrogen. Tetrakis(triphenylphosphine) palladium (20 mg) was added and the reaction mixture was heated in a microwave reactor at 150 C. for 30 min, filtered, and concentrated. The residue was subjected to gradient chromatography (MeOH/dichloromethane) to produce white powder, 56.4 mg (43% yield).1H NMR (400 MHz, CDCl3): delta 8.89 (s, 1H), 8.27 (br s, 1H); 7.89 (d, J=9.2 Hz, 1H); 7.59 (d, J=8.4, 2H); 7.52 (d, J=9.6 Hz, 1H); 7.36 (d, J=7.6, 2H).MS (ES+, m/z) 280.0 (base peak, M+H+); 581.0 (2M+Na+).

Reference： [1]Patent: US2011/21521,2011,A1 .Location in patent: Page/Page column 33

8
[ 1112983-31-9 ]
[ 108281-79-4 ]
[ 1313488-94-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5174 - 5184

9
[ 108281-79-4 ]
[ 1205896-23-6 ]

Reference： [1]Patent: US2011/263594,2011,A1

10
[ 108281-79-4 ]
[ 1205896-25-8 ]

Reference： [1]Patent: US2011/263594,2011,A1

11
1H-pyrazole-4-boronic acid [ No CAS ]
[ 108281-79-4 ]
[ 1205896-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; dimethyl sulfoxide; at 150℃; for 0.333333h;Microwave irradiation;	The compound can be prepared in the following way: 272 mg of (1H-pyrazol-4-yl)boronic acid are added to a mixture of 400 mg of <strong>[108281-79-4]6-bromo[1,2,4]triazolo[4,3-a]pyridine</strong> (commercial product), 8 ml of dimethyl sulphoxide, 69 mg of tetrakis(triphenylphosphine)palladium and 424 mg of sodium carbonate in solution in 2 ml of water. The reaction medium is microwave heated at 150 C. for 20 minutes. After a return to a temperature in the region of 20 C., the medium is concentrated by evaporation under reduced pressure, and then taken up with 40 ml of water. The aqueous phase is extracted with 3 times 20 ml of ethyl acetate. The precipitate formed in the aqueous phase is filtered off through sintered glass, washed with water, spin-filter-dried, and then dried. 200 mg of 6-(1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]-pyridine are thus obtained in the form of a white solid. MS: method A; [M+H]+ m/z=186; [M-H]- m/z=184; Tr=0.21 min.

Reference： [1]Patent: US2011/263594,2011,A1 .Location in patent: Page/Page column 20

12
[ 1401684-07-8 ]
[ 108281-79-4 ]
[ 1401683-44-0 ]

Yield	Reaction Conditions	Operation in experiment
11%		b) l-(3-([l,2,4]triazolo[4,3-a]pyridine-6-carbonyl)benzyl)quinazoline-2,4(lH,3H)-dione: To a solution of 6-bromo-[l,2,4]triazolo[4,3-a]pyridine (35 mg, 0.18mmol) in anhydrous THF (1 mL) was added «-BuLi (0.15 mL, 0.38 mmol) dropwise at -65C under N2, then it was maintained at this temperature for 3 h. To this solution was added dropwise a solution of 1- (3-(N-methoxy-N-methylcarbamoyl)benzyl)quinazoline-2,4(lH,3H)-dione (50 mg, 0.15 mmol) in THF (1 mL), then it was stirred for 4 h at -65 C. It was allowed to warm to 0 C for over 4 h. The reaction solution was poured into saturated aqueous H4C1, extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated. The crude product was purified by preparative TLC to give the title compound (6.5 mg, 11% yield) as white solid. 1H MR (CD30D+CDC13): 9.42 (d, J= 7.2 Hz, 1H), 8.41-8.39 (m, 2H), 8.10 (d, J= 7.2 Hz, 1H), 7.95 (d, J= 9.0 Hz, 1H), 7.58-7.45 (m, 4H), 7.18-7.11 (m, 3H), 5.38 (s, 2H). MS: m/z 398.2 [M+H]+.
11%		To a solution of <strong>[108281-79-4]6-bromo-[1,2,4]triazolo[4,3-a]pyridine</strong> (35 mg, 0.18 mmol) in anhydrous THF (1 mL) was added n-BuLi (0.15 mL, 0.38 mmol) dropwise at -65 C. under N2, then it was maintained at this temperature for 3 h. To this solution was added dropwise a solution of 1-(3-(N-methoxy-N-methylcarbamoyl)benzyl)quinazoline-2,4(1H,3H)-dione (50 mg, 0.15 mmol) in THF (1 mL), then it was stirred for 4 h at -65 C. It was allowed to warm to 0 C. for over 4 h. The reaction solution was poured into saturated aqueous NH4Cl, extracted with ethyl acetate (3*10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated. The crude product was purified by preparative TLC to give the title compound (6.5 mg, 11% yield) as white solid. 1H NMR (CD3OD+CDCl3): 9.42 (d, J=7.2 Hz, 1H), 8.41-8.39 (m, 2H), 8.10 (d, J=7.2 Hz, 1H), 7.95 (d, J=9.0 Hz, 1H), 7.58-7.45 (m, 4H), 7.18-7.11 (m, 3H), 5.38 (s, 2H). MS: m/z 398.2 [M+H]+.

Reference： [1]Patent: WO2012/130166,2012,A1 .Location in patent: Page/Page column 77
[2]Patent: US2014/23642,2014,A1 .Location in patent: Paragraph 0561

13
[ 1333340-17-2 ]
[ 108281-79-4 ]
[ 1426845-59-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In 1,4-dioxane; water; at 80 - 100℃; for 4h;Inert atmosphere;	Step 1 - Synthesis of 5-([ 1, 2, 4]triazolo[ 4, 3-a]pyridin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N- methylmethylsulfonamido)benzofuran-3-carboxamide To a degassed solution of 6-bromo-[l,2,4]triazolo[4,3-a]pyridine (177 mg, 0.90 mmol) and 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (300 mg, 0..60 mmol) in 1,4- dioxane (8 mL) and water (200 mu?) was added K3PO4 (380 mg, 1.79 mmol) and l, l'-Bis(di-tert- butylphosphino)ferrocene palladium dichloride (39 mg, 0.06 mmol) under N2 protection. The resulting mixture was heated to 80 C and stirred at this temperature for 2 hours, then heated to 100 C and stirred for 2 hours. The reaction was cooled, filtered through a pad of the celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-3% MeOH / DCM) to provide 5- ([l,2,4]triazolo [4,3-a pyridin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N- methylmethylsulfonamido) benzofuran-3-carboxamide] (230 mg, yield: 78%).

Reference： [1]Patent: WO2013/34048,2013,A1 .Location in patent: Page/Page column 94; 95

14
[ 108281-79-4 ]
[ 1426845-60-4 ]

Reference： [1]Patent: WO2013/34048,2013,A1

15
[ 108281-79-4 ]
[ 1426845-31-9 ]

Reference： [1]Patent: WO2013/34048,2013,A1

16
trans-2-(trifluoromethyl)cyclopropylboronic diester of N-methyliminodiacetic acid [ No CAS ]
[ 108281-79-4 ]
trans-6-(-2-(trifluoromethyl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyridine [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4284 - 4287

17
[ 108281-79-4 ]
[ 1609565-58-3 ]

Reference： [1]Patent: US2014/134133,2014,A1

18
[ 108281-79-4 ]
[ 1609565-56-1 ]

Reference： [1]Patent: US2014/134133,2014,A1

19
[ 1083326-73-1 ]
[ 108281-79-4 ]
[ 1609565-57-2 ]

Yield	Reaction Conditions	Operation in experiment
47.33%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	To a mixture of <strong>[108281-79-4]6-bromo-[1,2,4]triazolo[4,3-a]pyridine</strong> (3.00 g, 15.2 mmol) in 65 mL of 1,4-dioxane was added Pd(dppf)Cl2.CH2Cl2 (1.24 g, 1.52 mmol) and a solution of sodium carbonate (4.00 g, 38 mmol) in 13 mL of water, and the mixture was degassed and charged with N2 for 3 times, then stirred at rt for a while, followed by addition of 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide (7.78 g, 18.2 mmol), the mixture was degassed and charged with nitrogen for 3 times, then heated to 90 C. and stirred overnight. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a gray solid (3.00 g, 47.33%). MS (ESI, pos. ion) m/z: 418.1 [M+H]+; 1H NMR (600 MHz, CDCl3): delta 10.36 (s, 1H), 9.26 (s, 1H), 8.91 (s, 1H), 8.39 (d, J=2.3 Hz, 1H), 7.97 (d, J=2.3 Hz, 1H), 7.88 (d, J=9.5 Hz, 1H), 7.76 (td, J=8.5, 6.5 Hz, 1H), 7.70 (dd, J=9.6, 1.7 Hz, 1H), 7.61-7.54 (m, 1H), 7.24-7.15 (m, 1H), 3.64 (s, 3H).

Reference： [1]Patent: US2014/134133,2014,A1 .Location in patent: Paragraph 0454

20
[ 77992-44-0 ]
[ 122-51-0 ]
[ 108281-79-4 ]

Yield	Reaction Conditions	Operation in experiment
79.77%	With toluene-4-sulfonic acid; at 110℃; for 20h;	To a mixture of 5-bromo-2-hydrazinylpyridine (7.87 g, 42 mmol) in 200 mL of diethoxymethoxyethane was added p-toluenesulfonic acid (0.30 g, 1.7 mmol), and the mixture was heated to 110 C. and stirred further for 20 hours, then cooled to rt, and concentrated in vacuo. The residue was diluted with H2O (150 mL). The resulted mixture was washed with aqueous NaHCO3 solution (saturated, 40 mL), and extracted with DCM (300 mL*3). The combined organic phases were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a flash silica gel chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as a yellow solid (6.60 g, 79.77%). MS (ESI, pos. ion) m/z: 197.9 [M+H]+; 1H NMR (600 MHz, CDCl3): delta 8.82 (s, 1H), 8.34 (s, 1H), 7.75 (d, J=9.7 Hz, 1H), 7.36 (d, J=9.7 Hz, 1H).

Reference： [1]Patent: US2014/134133,2014,A1 .Location in patent: Paragraph 0451

21
[ 108281-79-4 ]
[ 1609565-59-4 ]

Reference： [1]Patent: US2014/134133,2014,A1

22
[ 236406-39-6 ]
[ 108281-79-4 ]
tert-butyl 2-([1,2,4]triazolo[4,3-α]pyridin-6-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 95℃; for 1h;Inert atmosphere; Microwave irradiation;	<strong>[236406-39-6]tert-butyl 2,8-diazaspiro[4.5]decane-8-carboxylate</strong> (0.200 g, 0.832 mmol), 6- bromo-[l,2,4]triazolo[4,3-a]pyridine (0.181 g, 0.915 mmol), cesium carbonate (0.407 mg, 1.25 mmol), Pd2(dba)3 (0.019 mg, 0.021 mmol), Xantphos (0.036 mg, 0.062 mmol), and 1,4-dioxane (3.0 mL) were charged to a microwave tube. The solution was degassed and filled with nitrogen (3X), then heated to 95C for 1 hour. The reaction was cooled to rt and concentrated in vacuo. The resulting residue was purified by prep TLC (5% MeOH/DCM) to provide tert-butyl 2- ([l,2,4]triazolo[4,3-a]pyridin-6-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate. LC-MS (IE, m/z): 358 [M+l]+.

Reference： [1]Patent: WO2016/60941,2016,A1 .Location in patent: Page/Page column 59

23
tert-butyl 4-(3-isopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-5-yl)piperi dine-1-carboxylate [ No CAS ]
[ 108281-79-4 ]
tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-isopropyl-1H-indol-5-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 90℃; for 2.5h;Inert atmosphere; Sealed tube;	To a solution of Template 2 (250 mg, 0.534 mmol), Fragment 1 (159 mg, 0.801 mmol), and [l,l'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (39.1 mg, 0.053 mmol) in dioxane (3.6 mL) was added 2M K3PO4 in water (0.80 mL, 1.60 mmol). The biphasic mixture was degassed with nitrogen for 10 min. The vial was sealed and stirred at 90 C for 2.5 hours. Upon completion, the reaction mixture was cooled to 25 C. The reaction mixture was diluted with water and precipitated solids were collected by vacuum filtration. The solid was triturated with isopropanol and ether to afford tert-butyl 4-(2-([l,2,4]triazolo[4,3-a]pyridin-6-yl)-3-isopropyl-lH-indol-5-yl)piperidine-l- carboxylate (237 mg, 0.516 mmol, 97% yield) as an off- white powder. LCMS retention time 0.95 min [TSl]. MS (ES+) m/z: 460.08 (M+H). NMR (400MHz, DMSO-de): 11.11 (s, IH), 9.35 (s, IH), 8.66 (s, IH), 7.90 (d, J=9.2 Hz, IH), 7.55 (s, IH), 7.50 (d, J=10.1Hz, IH), 7.30 (d, J=8.1Hz, IH), 7.02 (d, J=7.5 Hz, IH), 4.10 (d, J=10.8 Hz, 2H), 3.25 (s, IH), 2.94-2.69 (m, 3H), 1.80 (d, J=13.4 Hz, 2H), 1.65-1.48 (m, 2H), 1.47-1.38 (m, 15H).

Reference： [1]Patent: WO2019/28301,2019,A1 .Location in patent: Page/Page column 45-46

24
[ 108281-79-4 ]
[ 57260-71-6 ]
C₁₅H₂₁N₅O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 6392 - 6402

25
[ 4545-21-5 ]
[ 108281-79-4 ]
6-bromo-3-(1-phenylethyl)-[1,2,4]triazolo[4,3-a]pyridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7455 - 7460

26
[ 50-00-0 ]
[ 77992-44-0 ]
[ 108281-79-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7455 - 7460

27
[ 77992-44-0 ]
[ 68-12-2 ]
[ 108281-79-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With Imidazole hydrochloride; at 153℃;	General procedure: A mixture of 2-hydrazinylpyridine (0.5 mmol), imidazolium chloride (0.05 mmol) in DMF (2.0 mL) was stirred at 153 for 3-16 hours. The reaction was monitored by TLC. Upon completion, DMF was removed by rotary evaporator and the residue was applied for purification by flash column chromatography on silica gel to afford the desired product.

Reference： [1]Tetrahedron Letters,2020

28
[ 53939-30-3 ]
[ 108281-79-4 ]

Reference： [1]Tetrahedron Letters,2020

29
[ 108281-79-4 ]
[ 73183-34-3 ]
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.56%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 20 - 100℃; for 3h;Inert atmosphere;	Into a 40 mL vial were added 6-bromo- [1, 2, 4] triazolo [4, 3-a] pyridine (500 mg, 2.525 mmol, 1 equiv) and 4, 4, 5, 5-tetramethyl-2- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1, 3, 2-dioxaborolane (705.31 mg, 2.777 mmol, 1.1 equiv), AcOK (495.61 mg, 5.050 mmol, 2 equiv), Pd (dppf) Cl 2 (184.75 mg, 0.252 mmol, 0.1 equiv), dioxane (3 mL) at room temperature. Then the mixture was stirred at 100C under nitrogen atmosphere for 3 hours. The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 20: 1) to afford 6- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) - [1, 2, 4] triazolo [4, 3-a] pyridine (350 mg, 56.56%) as an off-white solid. LCMS: m/z (ESI), [M+H] + = 164.

Reference： [1]Patent: WO2020/52631,2020,A1 .Location in patent: Page/Page column 148-149

30
[ 108281-79-4 ]
7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-8-[[1,2,4]triazolo[4,3-a]pyridin-6-yl][1,2,4]triazolo[1,5-c]pyrimidin-5-amine [ No CAS ]

Reference： [1]Patent: WO2020/52631,2020,A1

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Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Williamson Ether Syntheses

Historical Records

Related Functional Groups of
[ 108281-79-4 ]

Bromides

[ 832735-60-1 ]

7-Bromo-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.90

[ 1253789-47-7 ]

6-Bromo-3-ethyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.89

[ 1190927-76-4 ]

7-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.89

[ 459448-06-7 ]

6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.85

[ 54230-90-9 ]

8-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.76

Related Parent Nucleus of
[ 108281-79-4 ]

Other Aromatic Heterocycles

[ 832735-60-1 ]

7-Bromo-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.90

[ 1253789-47-7 ]

6-Bromo-3-ethyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.89

[ 1190927-76-4 ]

7-Bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.89

[ 459448-06-7 ]

6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.85

[ 1004-65-5 ]

3-Methyl-[1,2,4]triazolo[4,3-a]pyridine

Similarity: 0.81

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{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

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[ CAS No. 108281-79-4 ] {[proInfo.proName]}

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[ 108281-79-4 ] Synthesis Path-Upstream 1~3

[ 108281-79-4 ] Synthesis Path-Downstream 1~30

Technical Information

Related Functional Groups of [ 108281-79-4 ]

Bromides

Related Parent Nucleus of [ 108281-79-4 ]

Other Aromatic Heterocycles

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[ 108281-79-4 ]

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[ 108281-79-4 ]