[ CAS No. 82090-52-6 ] {[proInfo.proName]}

Name: 82090-52-6|Imidazo[1,2-a]pyridin-2-ylmethanol|90%
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Quality Control of [ 82090-52-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 82090-52-6 ]

Product Details of [ 82090-52-6 ]

CAS No. :	82090-52-6	MDL No. :	MFCD06797471
Formula :	C₈H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ROPHYEIJSUUKEO-UHFFFAOYSA-N
M.W :	148.16	Pubchem ID :	2795540
Synonyms :

Calculated chemistry of [ 82090-52-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.32
TPSA :	37.53 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) :	-6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	0.38
Log Po/w (WLOGP) :	0.67
Log Po/w (MLOGP) :	0.17
Log Po/w (SILICOS-IT) :	0.78
Consensus Log Po/w :	0.75

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.54
Solubility :	4.3 mg/ml ; 0.029 mol/l
Class :	Very soluble
Log S (Ali) :	-0.73
Solubility :	27.4 mg/ml ; 0.185 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.9
Solubility :	1.89 mg/ml ; 0.0127 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 82090-52-6 ]

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 [ 82090-52-6 ]

* 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.

Downstream synthetic route of [ 82090-52-6 ]

[ 82090-52-6 ] Synthesis Path-Downstream 1~71

1
[ 82090-52-6 ]
[ 118000-43-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With manganese(IV) oxide; In chloroform; acetonitrile; for 22h;	A solution of imidazo[1 ,2-a]pyridin-2-ylmethanol (0.64 g, 4.32 mmol) in 1 :1 acetonitrile/chloroform (30 mL) was treated with manganese dioxide (4.51 g, 51.8 mmol) and stirred for 4 h. Another 0.37 g (4.32 mmol) manganese dioxide was added and the reaction was stirred 18 h. The mixture was filtered through a pad of Celite and washed thoroughly with chloroform and acetonitrile. The filtrate was concentrated to afford 0.35 g (51 %) of imidazo[1 ,2-a]pyridine-2-carbaldehyde as an off-white solid. 1H NMR (DMSO-Of6): delta 10.01 (s, 1H), 8.60 (m, 2H), 7.64 (m, 1H), 7.36 (m, 1H), 7.01 (t, 1H). MS m/z 147 (M+1).
15%	With manganese(IV) oxide; In ethanol; for 48h;Reflux;	c. Imidazo[1,2-a]pyridine-2-carbaldehyde To a solution of <strong>[82090-52-6]imidazo[1,2-a]pyridin-2-ylmethanol</strong> (3.0 g, 20 mmol) in EtOH (50 mL) was added manganese (IV) oxide (8.8 g, 100 mmol). The mixture was refluxed for 2 days. After cooling to room temperature, the mixture was filtered through Celite, and the filtrate was concentrated. The residue was purified by reverse phase column chromatography (eluting with acetonitrile in water 25% v/v, with 0.01% NH3. H2O) to afford the title compound (0.45 g, 15% yield) as a yellow solid. ESI MS: m/z 147 [M+H]+.
	With Dess-Martin periodane; In dichloromethane; at 20℃; for 2h;	[000822] To a solution of Compound 196C (6.9 g, 46.6 mmol) in DCM (140 mL) was added DMP (23.7 g, 55.9 mmol) at 0 C, then the mixture was stirred at room temperature for 2 h, then filtered. The filtrate was concentrated and the resulting residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 33% v/v) to furnish Compound 196D.

Reference： [1]Patent: WO2007/87548,2007,A2 .Location in patent: Page/Page column 47
[2]Patent: US2012/178748,2012,A1 .Location in patent: Page/Page column 49
[3]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 129 - 137
[4]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000822

2
[ 38922-77-9 ]
[ 82090-52-6 ]

Yield	Reaction Conditions	Operation in experiment
90%		b. Imidazo[1,2-a]pyridin-2-ylmethanol To an ice-cold solution of ethyl imidazo[1,2-a]pyridine-2-carboxylate (6.1 g, 32 mmol) in dry THF (300 mL) was added lithium aluminium hydride (LAH) (2.4 g, 64 mmol) in portions, and the temperature was maintained at <5 C. for 2 h. THF and water (50 mL, 1:1 v/v) were added slowly and the mixture was filtered. The filtrate was evaporated to dryness. The residue was re-dissolved in EtOAc (60 mL), and washed with brine (10 mL*3). The organic layers were combined, and the solvent was removed to give the title compound (4.3 g, yield 90%). ESI MS: m/z 149 [M+H]+.
86%	With sodium hydroxide; LiAlH4; In tetrahydrofuran; water;	Preparation of 2-hydroxymethyl-imidazo[1,2-a]pyridine LiAlH4 (1.4 g, 0.037 mol) was added in portions under stirring to a cooled (0C) mixture of imidazo [1,2-a]pyridine-2-carboxylic acid ethyl ester (9.0 g, 0.047 mol) dissolved in THF (140 ml). Stirring was continued for 1 hour. To the mixture were added under stirring (in the following order) H2O (1.4 ml) dropwise, 15% NaOH (1.4 ml) and H2O (4.2 ml). The precipitated salts were filtered off and washed with THF. The THF-solution was evaporated, giving the desired compound (6.0 g, 86%). The identity of the product was confirmed with NMR; delta(90 MHz; CDCl3) 4.90 (s, 2H), 6.65-6.90 (m, 1H), 7.05-7.30 (m, 1H), 7.50-7.70 (m, 2H), 8.10 (dd, 1H).
80%		A solution of ethyl imidazo[1,2-a]pyridine-2-carboxylate (2.01 g, 10.6 mmol) in 20 mL of a 1:1 mixture of THF and methanol was treated with lithium borohydride (15.9 mL, 2.0 M inTHF). After 1 h, another 15.9 mL lithium borohydride solution was added. The reaction was stirred for another 2.5 h, then treated with 10 mL of 1N sodium hydroxide. After stirring 5 min, the reaction was concentrated to remove most of the organic solvents.The mixture was diluted with brine and 10% aqueous sodium carbonate, then extracted with a 3:1 mixture of chloroform and isopropanol (3x). The combined organic layers were dried over Na2SO4 and concentrated. Hexane was added and the mixture was <n="48"/>concentrated. Purification by flash chromatography (silica gel, 0 to 10% methanol in dichloromethane) afforded 1.25 g (80%) of imidazo[1,2-a]pyridin-2-ylmethanol as a white solid. 1H NMR (CDCI3): delta 8.07 (d, 1H), 7.55 (m, 2H), 7.16 (m, 1H), 6.76 (t, 1H), 4.84 (s, 2H), 2.72 (broad, 1H).

33%		The imidazo [1, 2-a] pyridine-2-methanol used as starting material was prepared as follows:- To a mixture of imidazo[1, 2-a] pyridine-2-carboxylic acid ethyl ester (500 mg, 2.63 mmol) in THF (10 mL) at 5C was added 1M LiAIH4 in THF (2.63 mL, 2.63 mmol) dropwise under argon. The mixture was stirred at 5C for 1 h and then quenched by the addition of ethyl acetate (5 mL) and stirred for a further 15 min. The mixture was partitioned between DCM and water and the layers separated. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated at reduced pressure to give a yellow oil. This material was purified by silica column chromatography, eluting with a gradient of 0 to 10% methanol in DCM to give the title compound as a colourless oil (130 mg, 33%); NMR Spectrum: (CDC13) ; 3.30 (br s, 1H), 4.85 (s, 2H), 6.77 (t, 1H), 7.16 (1H, dt), 7.54 (1H, s), 7.57 (1H, s), 8. 08 (d, 1H).
	With lithium borohydride; sodium chloride; In tetrahydrofuran; methanol; water;	PREPARATION 20 Imidazo [1,2-a]pyridin-2-ylmethanol 3.68 g of lithium borohydride were added at room temperature to a solution of 9.17 g of ethyl imidazo[1,2-a]pyridine-2-carboxylate [described in J. Org. Chem., 30, 2403 -2407 (1965)]in 200 ml of tetrahydrofuran, and then 20 ml of methanol were added dropwise to the mixture, which was then allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was diluted with 10 ml of water and then concentrated by evaporation under reduced pressure. The concentrate was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of ethyl acetate and ethanol as the eluent. The product was then recrystallized from a mixture of ethyl acetate and hexane, to give 0.56 g of the title compound, melting at 126-128 C.
		Ethyl imidazo[l,2-a]pyridine-2-carboxylate (1.5g, 7.9 mmol) was dissolved in diethyl ether (30 niL) and dichloromethane (20 niL). Lithium aluminum hydride (450 mg, 11.8 mmol) was added at O0C, and the mixture was stirred 3 hours at room temperature. The reaction was quenched with an aqueous solution of sodium hydroxide and extracted 5 times with ethyl acetate. The cokmbined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, imidazo[l,2-a]pyridin-2-ylmethanol was obtained as a yellow oil (527 mg, 45% yield) and used in the next step without purification; 1H NMR (400 MHz, CDCl3): delta 4.86 (s, 2H), 6.76-6.80 (m, IH), 7.15-7.20 (m, IH), 7.55-7.58 (m, 2H), 8.09 (d, J = 6.8 Hz, IH).
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 0.5h;Inert atmosphere;	[000821] To a suspension of AlLiH4 (4.2 g, 111.3 mmol) in THF (200 mL) was added Compound 196B (10.7 g, 55.6 mmol) in THF (50 mL) dropwise at 0 C under nitrogen. Then the mixture was stirred at 0 C for 30 min, quenched with Na2S04.10H2O and filtered. The filtrate was concentrated to furnish the crude Compound 196C.

Reference： [1]Patent: US2012/178748,2012,A1 .Location in patent: Page/Page column 49
[2]Patent: EP242341,1987,A1
[3]Patent: WO2007/87548,2007,A2 .Location in patent: Page/Page column 46-47
[4]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362
[5]Patent: WO2005/61465,2005,A1 .Location in patent: Page/Page column 62
[6]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 129 - 137
[7]Patent: US5624935,1997,A
[8]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 133
[9]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000821

3
[ 82090-52-6 ]
[ 150556-72-2 ]
5-[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3052 - 3066

4
[ 82090-52-6 ]
[ 857350-35-7 ]