[ CAS No. 6188-25-6 ] {[proInfo.proName]}

Name: 6188-25-6|6-Chloroimidazo[1,2-a]pyridine|97%
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SKU: A108312
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Quality Control of [ 6188-25-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6188-25-6 ]

Product Details of [ 6188-25-6 ]

CAS No. :	6188-25-6	MDL No. :	MFCD05663807
Formula :	C₇H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XQEGYCZJSVFGEE-UHFFFAOYSA-N
M.W :	152.58	Pubchem ID :	2764328
Synonyms :

Calculated chemistry of [ 6188-25-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.2
TPSA :	17.3 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) :	-5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	2.39
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	1.32
Log Po/w (SILICOS-IT) :	1.63
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.96
Solubility :	0.168 mg/ml ; 0.0011 mol/l
Class :	Soluble
Log S (Ali) :	-2.39
Solubility :	0.615 mg/ml ; 0.00403 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.68
Solubility :	0.316 mg/ml ; 0.00207 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 6188-25-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6188-25-6 ]

* 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 [ 6188-25-6 ]
Downstream synthetic route of [ 6188-25-6 ]

[ 6188-25-6 ] Synthesis Path-Upstream 1~3

1
[ 107-20-0 ]
[ 1072-98-6 ]
[ 6188-25-6 ]

Yield	Reaction Conditions	Operation in experiment
5.10 g	at 80℃; for 16 h;	A mixture of A-1 (4.50 g, 35.00 mmol) and 2-chloroacetaldehyde (10.30 g, 52.50 mmol, 8.45 mL) in EtOH (50.00 mL) and H₂0 (10 mL) was stirred at 80 °C for 16 hours The mixture was concentrated to a residue that was diluted with 0 (100 mL) and extracted with EtOAc (150 mL x 2). The combined organic phase was washed with water (50 mL x 2) and brine (20 mL), dried over Na₂S0₄, filtered and concentrated to afford A-2 (5.10 g, 33.43 mmol) as a solid. H NMR (400 MHz, CDC1₃) δ_Η 8.18 (d, 1H), 7.65 (s, 1H), 7.59 - 7.50 (m, 2H), 7.12 (dd, 1H).

Reference： [1] Patent: WO2018/98500, 2018, A1, . Location in patent: Page/Page column 80; 81

2
[ 107-20-0 ]
[ 5350-93-6 ]
[ 6188-25-6 ]

Reference： [1] Patent: WO2009/50183, 2009, A2, . Location in patent: Page/Page column 118

3
[ 6188-25-6 ]
[ 885275-59-2 ]

Yield	Reaction Conditions	Operation in experiment
900 mg	With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 16 h;	To a mixture of A-2 (500.00 mg, 3.28 mmol) in DMF (10 mL) was added NIS (884.70 mg, 3.94 mmol) at 0 °C. The mixture was allowed to warm to 20 °C and stir for 16 hours. Sat.NaHCC (20 mL) was then added, and the mixture was stirred for 1 hour. The solid was collected by filtration and dried in oven to afford A-3 (900.00 mg, 3.23 mmol) as a solid. H NMR (400 MHz, CDC1₃) δ_Η 8.20 (s, 1H), 7.72 (s, 1H), 7.57 (d, 1H), 7.21 (dd, 1H).

Reference： [1] Patent: WO2018/98500, 2018, A1, . Location in patent: Page/Page column 80; 81

[ 6188-25-6 ] Synthesis Path-Downstream 1~68

Yield	Reaction Conditions	Operation in experiment
71%	In water; acetonitrile; for 6h;Reflux;	General procedure: 6-aminonicotinonitrile (10 g, 80 mmol) in acetonitrile (300 mL) was treated with a 50% aqueous solution of 2-chloroacetaldehyde (26.4 mL, 210 mmol). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. The mixture was concentrated to low bulk (approx. 100 mL), treated with saturated aqueous sodium hydrogencarbonate solution to neutral pH, and then extracted with dichloromethane (2 x 300 mL). The organic layer was dried (MgSO4) and evaporated and the residue was stirred with diethyl ether (200 mL), filtered and dried in vacuum to give the title compound (22.54 g, 94%) as a pale brown solid.LRMS (m/z): 144 (M+1)+.1H-NMR delta (CDCI3): 7.29 (dd, 1 H), 7.71 (d, 1 H), 7.73 (d, 1 H), 7.80 (d, 1 H), 8.61-8.62 (m, 1 H)

2
[ 626-55-1 ]
[ 6188-25-6 ]
6-chloro-3-(pyridin-3-yl)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Synlett,2006,p. 3237 - 3242
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7650 - 7655

3
[ 98546-51-1 ]
[ 6188-25-6 ]
[ 954373-61-6 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 7650 - 7655

4
[ 6188-25-6 ]
6-(4-(methylsulfanyl)phenyl)-3-(pyridin-3-yl)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 7650 - 7655
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7650 - 7655

5
[ 79-04-9 ]
[ 6188-25-6 ]
2-chloro-1-(6-chloroimidazo[1,2-a]pyridin-3-yl)ethanone monohydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;AlCl3; In methanol; CS2;	a) <strong>[6188-25-6]6-Chloro-imidazo[1,2-a]pyridine</strong> (0.1 mol) was dissolved in CS2 (400 ml). The solution was warrned. AlCl3 (0.3 mol) was added portionwise (exothermic temperature rise to reflux temperature). A solution of chloroacetyl chloride (0.2 mol) in CS2 (100 ml) was added dropwise and the reaction mixture was stirred and refluxed for 4 hours, then stirred overnight at room temperature. The mixture was decomposed with ice (200 g). CH3OH (100 ml) was added. 1N HCl (100 ml) was added and the mixture was stirred for 2 hours. The precipitate was filtered off, rinsed with 2-propanone and dried. Yield: 8.86 g of 2-chloro-1-(6-chloroimidazo[1,2-a]pyridin-3-yl)ethanone monohydrochloride (interm. 7). The filtrate was alkalized with Na2CO3, then with 50% NaOH.

Reference： [1]Patent: US2003/203897,2003,A1

6
7β-[2-(2-aminothiazol-4-yl)-2(Z)-ethoxyiminoacetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid [ No CAS ]
[ 6188-25-6 ]
7β-[2-(2-aminothiazol-4-yl)-2(Z)-ethoxyiminoacetamido]-3-[(6-chloroimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		7beta-[2-(2-Aminothiazol-4-yl)-2(Z)-ethoxyiminoacetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid is reacted with <strong>[6188-25-6]6-chloroimidazo[1,2-a]pyridine</strong> in the same manner as described in Example 2 to give the above-identified compound Elemental analysis for: C22 H20 N7 O5 S2 Cl.4H2 O: Calcd. (%): C, 41.67; H, 4.45; N, 15.46. Found (%): C, 41.85; H, 4.09; N: 15.69. IR spectrum numaxKBr cm-1: 1760, 1660, 1615, 1520, 1380. NMR spectrum (d6 -DMSO) delta: 1.19 (3H, t, J=7 Hz), 3.00 & 3.37 (2H, ABq, J=18 Hz), 4.06 (2H, q, J=7 Hz), 5.01 (1H, d, J=4.5 Hz), 5.27 & 5.50 (2H, ABq, J=14 Hz), 5.63 (1H, d. d, J=4.5 Hz & 8 Hz), 6.67 (1H, s), 7.16 (2H, br. s), 8.00-8.19 (1H, m), 8.26-8.44 (1H, m), 8.25-8.64 (1H, m), 8.66-8.86 (1H, m), 9.43 (1H, d, J=8 Hz).

Reference： [1]Patent: US4788185,1988,A

7
3-(3-Oxobutyryloxymethyl)-7β-[2-(2-tritylaminothiazol-4-yl)-2(Z)-(1-methyl-1tert-butoxycarbonylethoxyimino)acetamido]-3-cephem-4-carboxylic acid [ No CAS ]
[ 6188-25-6 ]
7β-[2-(2-Aminothiazol-4-yl)-2(Z)-(1-carboxy-1-methylethoxyimino)acetamido]-3-[(6-chloroimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3-(3-Oxobutyryloxymethyl)-7beta-[2-(2-tritylaminothiazol-4-yl)-2(Z)-(1-methyl-1tert-butoxycarbonylethoxyimino)acetamido]-3-cephem-4-carboxylic acid is reacted with <strong>[6188-25-6]6-chloroimidazo[1,2-a]pyridine</strong> in the same manner as described in Example 5 to give the above-identified compound Elemental anslysis for: C22 H20 N7 O5 S2 Cl.4H2 O: Calcd. (%): C, 41.68; H, 4.45; N, 15.47. Found (%): C, 41.42; H, 4.67; N, 15.42. IR spectrum numaxKBr cm-1: 1760, 1610, 1520. NMR spectrum (d6 -DMSO) delta: 1.38 (3H, s), 1.42 (3H, s), 3.01 (2H, ABq, J=18 Hz), 4.97 (1H, d, J=4.8 Hz), 5.20-5.52 (2H, m), 5.60-5.79 (1H, m), 6.67 (1H, s), 7.10 (2H, br. s), 7.96-8.16 (1H, m), 8.30-8.80 (3H, m), 9.32 (1H, s), 11.45 (1H, d, J=9 Hz).

Reference： [1]Patent: US4788185,1988,A

8
7β-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-(carboxymethoxyimino)acetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid [ No CAS ]
[ 6188-25-6 ]
7β-[2-(2-Amino-5-chlorothiazol-4-yl)-2(Z)-(carboxymethoxyimino)acetamido]-3-[(6-chloroimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate monosodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; sodium hydrogencarbonate; In water; acetone; acetonitrile;	(ii) The whole amount of 7beta-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-(carboxymethoxyimino)acetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid, 2.5 g of <strong>[6188-25-6]6-chloroimidazo[1,2-a]pyridine</strong> and 2 g of sodium iodide are mixed in 20 ml of 50% acetonitrile in water and the mixture is heated at 70 C. for 90 minutes with stirring, and then cooled to room temperature. Two grams of sodium bicarbonate is added to the reaction mixture and the mixture is chromatographed on a column of silica gel (50 g). The column is washed with 0.3 l of acetone and then with 0.5 l of acetone:water=8:1 and the product is then eluted with acetone:water=5:2. Fractions containing the objective compound are concentrated and the residue is placed on a column of Sephadex LH-20 (Pharmacia Inc., Sweden) and eluted with water. Fractions containing the objective compound are lyophilized to give the above-identified compound. Elemental analysis for C22 H16 Cl2 N7 NaO7 S2.2H2 O: Calcd.(%): C, 38.60; H, 2.95; N, 14.33. Found (%): C, 38.40; H, 2.99; N, 14.06. IR spectrum numaxKBr cm-1: 1770, 1680, 1620, 1520, 1440, 1320. NMR spectrum (d6 -DMSO)delta: 2.04 and 3.40(2H, ABq, J=18 Hz), 4.25(2H, br.s), 4.97(1H, d, J=5 Hz), 5.40(2H, br.s), 5.66(1H, d. d, J=5 Hz and 8 Hz), 7.31(2H, br.s), 8.05(1H, d, J=6 Hz), 8.40(1H, d, J=3 Hz), 8.58(1H, d, J=7 Hz), 9.28(1H, br. s), 9.77(1H, d, J=6 Hz).

Reference： [1]Patent: US4788185,1988,A

9
[ 100-39-0 ]
[ 6188-25-6 ]
1-benzyl-6-chloroimidazo[1,2-a]pyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; acetonitrile;	EXAMPLE 7 1-Benzyl-6-chloroimidazo[1,2-a]pyridinium bromide A solution of 2.3 g. of <strong>[6188-25-6]6-chloroimidazo[1,2-a]pyridine</strong> and 3.42 g. of alpha-bromotoluene in 40 ml. of dry acetonitrile is heated at reflux temperatures overnight. The solution is cooled and 35 ml. of diethyl ether added. The precipitated solids are collected and twice recrystallized from isopropanoldiethyl ether, 3.8 g., m.p. 193-195 C. Anal. Calc'd for C14 H12 N2 ClBr: C, 52.0; H, 3.7; N, 8.7. Found: C, 52.0; H, 3.8; N, 8.8.
	In diethyl ether; acetonitrile;	EXAMPLE 7 1-Benzyl-6-chloroimidazo[1,2-a]pyridinium bromide A solution of 2.3 g. of <strong>[6188-25-6]6-chloroimidazo[1,2-a]pyridine</strong> and 3.42 g. of alpha-bromotoluene in 40 ml. of dry acetonitrile is heated at reflux temperatures overnight. The solution is cooled and 35 ml. of diethyl ether added. The precipitated solids are collected and twice recrystallized from isopropanoldiethyl ether, 3.8 g., m.p. 193-195 C. Anal. Calc'd for C14 H12 N2 ClBr: C, 52.0; H, 3.7; N, 8.7; Found: C, 52.0; H, 3.8; N, 8.8.

Reference： [1]Patent: US4097598,1978,A
[2]Patent: US4044015,1977,A

10
[ 676239-97-7 ]
[ 6188-25-6 ]
[ 930113-24-9 ]

Reference： [1]Synlett,2006,p. 3237 - 3242

11
[ 108-86-1 ]
[ 6188-25-6 ]
[ 930113-27-2 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342
[2]Synlett,2006,p. 3237 - 3242

12
[ 591-17-3 ]
[ 6188-25-6 ]
[ 930113-21-6 ]

Reference： [1]Synlett,2006,p. 3237 - 3242

13
[ 5111-65-9 ]
[ 6188-25-6 ]
[ 930113-22-7 ]

Reference： [1]Synlett,2006,p. 3237 - 3242

14
[ 557-93-7 ]
[ 6188-25-6 ]
[ 1080429-96-4 ]

Reference： [1]Synthesis,2008,p. 2537 - 2542

15
[ 3017-69-4 ]
[ 6188-25-6 ]
[ 1080430-00-7 ]

Reference： [1]Synthesis,2008,p. 2537 - 2542

16
[ 98-81-7 ]
[ 6188-25-6 ]
[ 1080430-04-1 ]

Reference： [1]Synthesis,2008,p. 2537 - 2542

17
[ 1607-57-4 ]
[ 6188-25-6 ]
[ 1080430-08-5 ]

Reference： [1]Synthesis,2008,p. 2537 - 2542

18
[ 6188-25-6 ]
[ 21428-17-1 ]
[ 1080430-11-0 ]

Reference： [1]Synthesis,2008,p. 2537 - 2542

19
[ 6188-25-6 ]
[ 886371-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In acetic acid; at 20.0℃; for 1.0h;	To 6-chloro-imidazo[1,2-a]pyridine (1 eq, 253 mmol, 39 g) in acetic acid (500 ml) under inert atmosphere, is added dropwise bromine (1 eq, 253 mmol, 13 ml). After 1 hour stirring at room temperature, the reaction mixture is filtered and to give a beige solid (64 g) 3-Bromo-6-chloro-imidazo[1,2-a]pyridine hydrobromide;[M+H]+ 232(234)

Reference： [1]Patent: WO2009/50183,2009,A2 .Location in patent: Page/Page column 118

20
[ 107-20-0 ]
[ 5350-93-6 ]
[ 6188-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; for 3h;Heating / reflux;	To a solution of 50% aq. chloroacetaldehyde (1.1 eq, 291 mmol, 37 ml) in ethanol (700 ml) is added 3-amino-6-chloro-pyridine (1 eq, 264 mmol, 34 g) at room temperature. The reaction mixture is refluxed for 3 hours. The solvent is removed in vacuo and the crude product is dissolved in water (400 ml). The aqueous solution is treated with sodium bicarbonate to pH = 8 and extracted with dcm (3 x 250 ml), the organic layer is dried (MgStheta4) and evaporated to give a brown solid (39.2 g) 6-chloro- imidazo[1,2-a]pyridine; [M+H]+ 153(155)

Reference： [1]Patent: WO2009/50183,2009,A2 .Location in patent: Page/Page column 118

21
[ 1663-39-4 ]
[ 6188-25-6 ]
[ 1116088-98-2 ]

Reference： [1]Synthesis,2009,p. 271 - 276

22
[ 292638-85-8 ]
[ 6188-25-6 ]
methyl (2E)-3-(6-chloroimidazo[1,2-a]pyridin-3-yl)acrylate [ No CAS ]

Reference： [1]Synthesis,2009,p. 271 - 276

23
[ 1207852-36-5 ]
[ 6188-25-6 ]
[ 1207853-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; triphenylphosphine;palladium diacetate; In 1,4-dioxane; at 130℃; for 0.5h;Microwave irradiation;	Preparation of compound 5a: (3R)-Tert-butyl 3-(6-(6-chloroimidazo[1,2- a]pyridin-3-yl)pyrazin-2-ylamino)piperidine-1 -carboxylateA mixture of 6-chloroimidazo[1 ,2-a]pyridine (100 mg, 0.66 mmol), 1a (308 mg, 0.98 mmol), palladium (II) acetate (30 mg, 0.13 mmol), triphenylphosphine (17 mg, 0.07 mmol), and potassium carbonate (90 mg, 0.66 mmol) in dioxane (1.2 mL) was heated in a microwave at 130 0C for 30 min. The reaction was filtered and purified by preparative reverse phase HPLC (water-acetonithle with acetic acid), which gave 5a.

Reference： [1]Patent: WO2010/16005,2010,A1 .Location in patent: Page/Page column 85-86

24
[ 106-39-8 ]
[ 6188-25-6 ]
[ 1467063-99-5 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

25
[ 108-37-2 ]
[ 6188-25-6 ]
[ 1467064-00-1 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

26
[ 694-80-4 ]
[ 6188-25-6 ]
[ 1467064-01-2 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

27
[ 1073-06-9 ]
[ 6188-25-6 ]
[ 1467064-02-3 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

28
[ 17763-67-6 ]
[ 6188-25-6 ]
[ 930113-27-2 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

29
[ 29540-84-9 ]
[ 6188-25-6 ]
[ 1467063-99-5 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2340 - 2342

30
[ 1679-18-1 ]
[ 6188-25-6 ]
[ 1467063-99-5 ]

Reference： [1]Catalysis Communications,2014,vol. 56,p. 65 - 67

31
[ 6188-25-6 ]
[ 98-80-6 ]
[ 930113-27-2 ]

Reference： [1]Catalysis Communications,2014,vol. 56,p. 65 - 67

32
[ 6188-25-6 ]
[ 112-55-0 ]
C₁₉H₂₉ClN₂S [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 22356 - 22360

33
[ 109-79-5 ]
[ 6188-25-6 ]
C₁₁H₁₃ClN₂S [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 22356 - 22360

34
[ 100-53-8 ]
[ 6188-25-6 ]
C₁₄H₁₁ClN₂S [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 22356 - 22360

35
[ 107-03-9 ]
[ 6188-25-6 ]
C₁₀H₁₁ClN₂S [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 22356 - 22360

36
[ 6188-25-6 ]
6-chloro-3-(6-chloro-imidazo[1,2-a]pyridin-3-yl)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3109 - 3114

37
[ 6188-25-6 ]
[ 67-64-1 ]
1-(6-chloroimidazo[1,2-a]pyridin-3-yl)propane-1,2-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 12725 - 12732

38
[ 98-86-2 ]
[ 6188-25-6 ]
1-(6-chloroimidazo[1,2-a]pyridin-3-yl)-2-phenylethane-1,2-dione [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 67 - 73
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 4991 - 4997

39
[ 109-06-8 ]
[ 6188-25-6 ]
(6-chloroimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3582 - 3585

40
[ 1679-18-1 ]
[ 6188-25-6 ]
6-chloro-3-((4-chlorophenyl)thio)imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 7771 - 7783

41
[ 100-58-3 ]
[ 6188-25-6 ]
[ 328062-45-9 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5312 - 5315

42
[ 6188-25-6 ]
6-deuterioimidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 8934 - 8946

43
[ 89-98-5 ]
[ 6188-25-6 ]
6H-benzo[b]imidazo[5,1,2-de]quinolizin-6-one [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5260 - 5263

44
[ 1206599-46-3 ]
[ 6188-25-6 ]
6-chloro-3-(3-chloro-4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With palladium diacetate; potassium hydroxide; In water; at 100℃; for 24h;Inert atmosphere;	General procedure: The mixture of 1 (0.1g), 2/2'/2"(1.5 equivalent), Pd(OAc)2 (5 mol%), KOH (3 equivalent) in 4 mL of nitrogen purged deionised water were stirred at 100 C. The reaction was carried out under nitrogen atmosphere. The progress of reaction was monitored using TLC. Upon completion of the reaction, silica gel was added and the mixture was evaporated under vacuum. The resulted mixture was purified by column chromatography using EtOAc:Petroleum ether (0.4:0.6 to 0.8:0.2, EtOAc:Petroleum ether) to afford pure 3-aryl imidazo[1,2-a]pyridines 3 and 4.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2818 - 2821

45
[ 624-31-7 ]
[ 6188-25-6 ]
6-chloro-3-(p-tolyl)imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With palladium diacetate; potassium hydroxide; In water; at 100℃; for 24h;Inert atmosphere;	General procedure: The mixture of 1 (0.1g), 2/2'/2"(1.5 equivalent), Pd(OAc)2 (5 mol%), KOH (3 equivalent) in 4 mL of nitrogen purged deionised water were stirred at 100 C. The reaction was carried out under nitrogen atmosphere. The progress of reaction was monitored using TLC. Upon completion of the reaction, silica gel was added and the mixture was evaporated under vacuum. The resulted mixture was purified by column chromatography using EtOAc:Petroleum ether (0.4:0.6 to 0.8:0.2, EtOAc:Petroleum ether) to afford pure 3-aryl imidazo[1,2-a]pyridines 3 and 4.

Reference： [1]European Journal of Organic Chemistry,2020,vol. 2020,p. 1823 - 1827
[2]Tetrahedron Letters,2017,vol. 58,p. 2818 - 2821

46
[ 6188-25-6 ]
C₇H₄Cl₂N₂ [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 5058 - 5062

47
[ 107-20-0 ]
[ 1072-98-6 ]
[ 6188-25-6 ]

Yield	Reaction Conditions	Operation in experiment
5.10 g	In ethanol; water; at 80℃; for 16h;	A mixture of A-1 (4.50 g, 35.00 mmol) and 2-chloroacetaldehyde (10.30 g, 52.50 mmol, 8.45 mL) in EtOH (50.00 mL) and H20 (10 mL) was stirred at 80 C for 16 hours The mixture was concentrated to a residue that was diluted with 0 (100 mL) and extracted with EtOAc (150 mL x 2). The combined organic phase was washed with water (50 mL x 2) and brine (20 mL), dried over Na2S04, filtered and concentrated to afford A-2 (5.10 g, 33.43 mmol) as a solid. H NMR (400 MHz, CDC13) deltaEta 8.18 (d, 1H), 7.65 (s, 1H), 7.59 - 7.50 (m, 2H), 7.12 (dd, 1H).

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 80; 81

48
[ 6188-25-6 ]
C₁₆H₁₀F₆N₂O₂ [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

49
[ 6188-25-6 ]
C₁₅H₉F₆N₃O [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

50
[ 6188-25-6 ]
C₁₈H₁₉F₃N₂O [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

51
[ 6188-25-6 ]
C₁₈H₁₂F₃N₃ [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

52
[ 6188-25-6 ]
[ 885275-59-2 ]

Yield	Reaction Conditions	Operation in experiment
900 mg	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 16.0h;	To a mixture of A-2 (500.00 mg, 3.28 mmol) in DMF (10 mL) was added NIS (884.70 mg, 3.94 mmol) at 0 C. The mixture was allowed to warm to 20 C and stir for 16 hours. Sat.NaHCC (20 mL) was then added, and the mixture was stirred for 1 hour. The solid was collected by filtration and dried in oven to afford A-3 (900.00 mg, 3.23 mmol) as a solid. H NMR (400 MHz, CDC13) deltaEta 8.20 (s, 1H), 7.72 (s, 1H), 7.57 (d, 1H), 7.21 (dd, 1H).

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 80; 81

53
[ 6188-25-6 ]
C₈H₄ClF₃N₂ [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

54
[ 6188-25-6 ]
C₁₅H₈F₆N₂O [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

55
[ 6188-25-6 ]
[ 139301-27-2 ]
C₁₄H₉F₃N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.55 mg	With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; In 1,4-dioxane; water; at 80℃; for 16h;	A mixture of [4-(trifluoromethoxy)phenyllboronic acid (202.45 mg, 983.08 pmol), A-2 (100.0mg, 655.39 pmol), Pd(t-Bu3P)2 (33.49 mg, 65.54 pmol) and K3P04 (278.24 mg, 1.31 mmol) indioxane (10 mL) and H20 (1 mL) was stirred at 80 C for 16 hours, at which point the desiredproduct was observed by LCMS. The mixture was then concentrated to give the crude product,which was purified by Prep-HPLC to afford Compound 6 (38.55 mg) as a solid. 1H NMR (400MHz, CDCl3) oe11 8.30 (s, 1H), 7.74 - 7.63 (m, 3H), 7.58 (d, 2H), 7.39 (br d, 1H), 7.33 (br d, 2H).LCMS R = 0.98 1 mm in 2.0 mm chromatography, MS ESI calcd. for C,4H,0F3N20 [M+H1 279.1, found 278.9.

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 83; 84

56
[ 504-29-0 ]
[ 75-91-2 ]
[ 6188-25-6 ]
N-((6-chloroimidazo[1,2-a]pyridin-3-yl)methyl)pyridin-2-amine [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2018,vol. 16,p. 8620 - 8628

57
[ 67-56-1 ]
[ 558-13-4 ]
[ 6188-25-6 ]
methyl 6-chloroimidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 9869 - 9896

58
[ 10544-50-0 ]
[ 5122-99-6 ]
[ 6188-25-6 ]
(6-chloroimidazo[1,2-a]pyridine-2,3-diyl)bis(sulfanediyl)bis(4,1-phenylene)diboronic acid [ No CAS ]