[ CAS No. 136117-69-6 ]

Name: 136117-69-6|Methyl imidazo[1,2-a]pyridine-6-carboxylate|98%
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Product Details of [ 136117-69-6 ]

CAS No. :	136117-69-6	MDL No. :	MFCD06200984
Formula :	C₉H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTDBMFODXFTFIL-UHFFFAOYSA-N
M.W :	176.17 g/mol	Pubchem ID :	2764326
Synonyms :

Safety of [ 136117-69-6 ]

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
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Application In Synthesis of [ 136117-69-6 ]

* 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 [ 136117-69-6 ]
Downstream synthetic route of [ 136117-69-6 ]

[ 136117-69-6 ] Synthesis Path-Upstream 1~5

1
[ 136117-69-6 ]
[ 132213-07-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6586 - 6590

2
[ 136117-69-6 ]
[ 106730-54-5 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 6, p. 1556 - 1567

3
[ 136117-69-6 ]
[ 139022-25-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 465 - 469
[2] Patent: WO2006/15737, 2006, A1, . Location in patent: Page/Page column 51-52

4
[ 136117-69-6 ]
[ 886361-98-4 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 947 - 950
[2] Patent: WO2009/50183, 2009, A2, . Location in patent: Page/Page column 122

5
[ 136117-69-6 ]
[ 1313725-89-1 ]
[ 1313725-88-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7577 - 7589

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Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With sodium hydride In toluene; mineral oil at 80℃; Stage #2: acetonitrile In toluene at 80℃; Stage #3: With hydrogenchloride In water; toluene	General procedure for aryl/heteroaryl β-ketonitrile synthesis (Al):[0149] Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.[0150] To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 80 °C and then dry CH3CN was added dropwise (1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[0151] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2 N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM. [0152] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; 3-Imidazo[l, 2-aJpyridin- 6-yl-3-oxo-propionitrile[0159] The product was obtained starting from imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester according to general procedure Al :Yield 39%C10H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=O.23, 100% (3 min method)1H-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (1H, m), 8.07 (1H, s), 9.40 (s, 1H).
	Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate; acetonitrile With sodium hydride In toluene at 80℃; for 18h; Stage #2: With hydrogenchloride; water In toluene at 20℃;	To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 800C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.
	Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate With sodium hydride In toluene; mineral oil at 80℃; Heating / reflux; Stage #2: acetonitrile In toluene; mineral oil at 80℃; for 18h; Stage #3: With hydrogenchloride In water	Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully added. The mixture was heated at 80 0C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[00164] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.[00165] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; The product was obtained starting from imidazo[l,2-a]pyridine-6- carboxylic acid methyl ester according to general procedure AlYield 39%Ci0H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=0.23, 100% (3 min method)IH-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (IH, m), 8.07 (IH, s), 9.40 (s,IH).

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid;Heating / reflux;	General procedure for aryl/heteroaryl beta-ketonitrile synthesis (Al):Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 niL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was <n="42"/>evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.
		Aryl or heteroaryl methyl carboxylate were commercially available or were synthesized according to the following standard procedure: the aryl or heteroaryl carboxylic acid (32 mmol) was dissolved in MeOH (40 mL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated aqueous NaHCO3 solution. The organic phase was dried and evaporated under reduced pressure, and the crude was used without further purification.To a solution of an aryl or heteroaryl methyl carboxylate (6.5 mmol) in dry toluene (6 mL) under N2, NaH (50-60% dispersion in mineral oil, 624 mg, 13 mmol) was carefully <n="41"/>added. The mixture was heated at 80 0C and then dry CH3CN was added dropwise(1.6 mL, 30.8 mmol). The reaction was heated for 18 hours and generally the product precipitated from the reaction mixture as Na salt.[00164] The reaction was then allowed to cool down to room temperature and the solid formed was filtered and then dissolved in water. The solution was then acidified with 2N HCl solution and at pH between 2-6 (depending on the ring substitution on the aryl/heteroaryl system) the product precipitated and was filtered off. If no precipitation occurred, the product was extracted with DCM.[00165] After work-up, the products were generally used in the following step without further purification. The general yield was between 40 and 80%.; The product was obtained starting from imidazo[l,2-a]pyridine-6- carboxylic acid methyl ester according to general procedure AlYield 39%Ci0H7N3O Mass (calculated) [185]; (found) [M+H+]=186 [M-H]=I 84LC Rt=0.23, 100% (3 min method)IH-NMR: (dmso-d6): 4.72 (2H,s), 7.61-7.65 (2H, m), 7.70 (IH, m), 8.07 (IH, s), 9.40 (s,IH).

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydrogencarbonate In methanol for 8h; Reflux;
63%	In ethanol; water for 4h; Reflux;
	In ethanol for 18h; Heating / reflux;	N1 To a solution of 50% aq. chloroacetaldehyde (1.1 eq, 36 mmol, 4.6 ml) in ethanol (120 ml) is added 6-amino-nicotinic acid methyl ester (1 eq, 33 mmol, 5 g) at room temperature. The reaction mixture is heated at reflux for 18 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 (MgSO4) and evaporated to give the title compound as a beige solid.

	Stage #1: 2-chloroethanal; methyl 6-aminonicotinoate In ethanol; water for 4h; Reflux; Stage #2: With sodium hydrogencarbonate In water	To a solution of Z-1 (9.0 g, 59.21 mmol) in anhydrous EtOH (160 ml) was added chloroacetaldehyde (40% in H2O, 48.6 mL, 296 mmol). The reaction mixture was refluxed for 4h, then concentrated. The residue was dissolved in water and adjusted to pH>7 with a saturated NaHC03 solution, extracted with EtOAc and purified by silica gel chromatography to afford the title compound (6.60 g). MS (m/z): 177 (M+1 )+.
	In ethanol; water for 4h; Reflux;	Methyl H-imidazo[1,2-a]pyridine-6-carboxylate (Z-2) To a solution of Z-1 (9.0 g, 59.21 mmol) in anhydrous EtOH (160 ml) was added chloroacetaldehyde (40% in H2O, 48.6 mL, 296 mmol). The reaction mixture was refluxed for 4 h, then concentrated. The residue was dissolved in water and adjusted to pH>7 with a saturated NaHCO3 solution, extracted with EtOAc and purified by silica gel chromatography to afford the title compound (6.60 g). MS (m/z): 177 (M+1)+.

[ CAS No. 136117-69-6 ]

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[ 136117-69-6 ] Synthesis Path-Upstream 1~5

[ 136117-69-6 ] Synthesis Path-Downstream 1~43

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[ 136117-69-6 ]

Esters

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[ 136117-69-6 ]

Other Aromatic Heterocycles

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Yield	Reaction Conditions	Operation in experiment
80%	With isopropylmagnesium chloride In tetrahydrofuran at -20℃; for 1h; Inert atmosphere;
	Stage #1: methyl 6-imidazo<1,2-a>pyridinecarboxylate; N,0-dimethylhydroxylamine With isopropylmagnesium bromide In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water	To a mixture of Z-2 (5.0 g, 28.4 mmol) and N-methoxymethanamine (5.54 g, 56.8 mmol) in dry THF (50 ml) at -20°C under N2 was added isopropylmagnesium chloride (56.8 mL, 1 13.6 mmol) over 30 mins. The resulting mixture was stirred at -20°C for 30 mins, then quenched with 20% N H4CI solution, and extracted with EtOAc (50 mL *3). The combined organic layers were dried over Na2S04, concentrated and purified by silicon gel chromatography to afford the title compound (3.0 g). MS (m/z): 206 (M+1 )+.
	With isopropylmagnesium chloride In tetrahydrofuran at -20℃; for 1h; Inert atmosphere;	N-Methoxy-N-methylH-imidazo[1,2-a]pyridine-6-carboxamide (Z-3) To a mixture of Z-2 (5.0 g, 28.4 mmol) and N-methoxymethanamine (5.54 g, 56.8 mmol) in dry THF (50 ml) at -20° C. under N2 was added isopropylmagnesium chloride (56.8 mL, 113.6 mmol) over 30 mins. The resulting mixture was stirred at -20° C. for 30 mins, then quenched with 20% NH4Cl solution, and extracted with EtOAc (50 mL*3). The combined organic layers were dried over Na2SO4, concentrated and purified by silicon gel chromatography to afford the title compound (3.0 g). MS (m/z): 206 (M+1)+.

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[ CAS No. 136117-69-6 ]

Quality Control of [ 136117-69-6 ]

Related Doc. of [ 136117-69-6 ]

Product Details of [ 136117-69-6 ]

Safety of [ 136117-69-6 ]

Application In Synthesis of [ 136117-69-6 ]

[ 136117-69-6 ] Synthesis Path-Upstream 1~5

[ 136117-69-6 ] Synthesis Path-Downstream 1~43

Related Functional Groups of [ 136117-69-6 ]

Esters

Related Parent Nucleus of [ 136117-69-6 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

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Related Functional Groups of
[ 136117-69-6 ]

Related Parent Nucleus of
[ 136117-69-6 ]