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Inhibitors/Agonists
Stapled Peptide
PKA/AKAP (stapled peptide)
7-Methylimidazo[1,2-a]pyridine
Inhibitors/Agonists
Stapled Peptide
PKA/AKAP (stapled peptide)

[ CAS No. 874-39-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 874-39-5
Chemical Structure| 874-39-5
Chemical Structure| 874-39-5
Structure of 874-39-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 874-39-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 874-39-5 ]

SDS Specification
Alternatived Products of [ 874-39-5 ]

Product Details of [ 874-39-5 ]

CAS No. :874-39-5 MDL No. :MFCD06761695
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :IQDUNRGHZFBKLT-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :136681
Synonyms :

Calculated chemistry of [ 874-39-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.16
TPSA : 17.3 Ų

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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.45
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.284 mg/ml ; 0.00215 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 0.992 mg/ml ; 0.0075 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.483 mg/ml ; 0.00366 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 874-39-5 ]

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 [ 874-39-5 ]

* 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 [ 874-39-5 ]

[ 874-39-5 ] Synthesis Path-Downstream   1~76

  • 1
  • [ 695-34-1 ]
  • [ 107-20-0 ]
  • [ 874-39-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water for 72h; Ambient temperature;
With sodium hydrogencarbonate In ethanol for 2h; Heating / reflux; AA.1 Proced "ure AA1 - Imidazopyridine ring formation; To a solution of a 4-substitued-pyridin-2-ylamine (1.0 equiv) in EtOH was added NaHCO3 (2.0 equiv) followed by chloroacetaldehyde (1.5 equiv). The mixture was refluxed for 2 h. Solvents were removed under reduced pressure and the crude mixture was partitioned between water and EtOAc. The products were purified using column chromatography, trituration or recrystallisation.
With sodium hydrogencarbonate In ethanol; water at 80℃; for 2h;
In ethanol Reflux;

Reference： [1]Kaiser; Spagnuolo; Adams Jr.; Audia; Dupont; Hatoum; Lowe; Prosser; Sturm; Noronha-Blob [Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4415 - 4424]
[2]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2008/78100, 2008, A2 Location in patent: Page/Page column 125
[3]Mu, Bing; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Chang, Junbiao; Wu, Yangjie [Organic Letters, 2016, vol. 18, # 20, p. 5260 - 5263]
[4]Juillet, Charlotte; Ermolenko, Ludmila; Boyarskaya, Dina; Baratte, Blandine; Josselin, Béatrice; Nedev, Hristo; Bach, Stéphane; Iorga, Bogdan I.; Bignon, Jérôme; Ruchaud, Sandrine; Al-Mourabit, Ali [Journal of Medicinal Chemistry, 2021, vol. 64, # 2, p. 1197 - 1219]
  • 2
  • [ 137415-94-2 ]
  • [ 874-39-5 ]
  • 7-Methyl-1-(5-oxo-4,4-diphenyl-tetrahydro-furan-2-ylmethyl)-1H-imidazo[1,2-a]pyridin-4-ylium; chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With IRA-400(Cl) resin 1.) CH2Cl2, 120 deg C, 16 h, 2.) CH3OH;
Reference： [1]Kaiser; Spagnuolo; Adams Jr.; Audia; Dupont; Hatoum; Lowe; Prosser; Sturm; Noronha-Blob [Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4415 - 4424]
  • 3
  • [ 874-39-5 ]
  • [ 74-88-4 ]
  • [ 15639-33-5 ]
YieldReaction ConditionsOperation in experiment
In nitrobenzene
Reference： [1]Maury, G.; Pigiere, C. [Tetrahedron, 1981, vol. 37, p. 83 - 90] Maury, G.; Pigiere, C. [Tetrahedron, 1981, vol. 37, p. 91 - 95]
  • 4
  • [ 874-39-5 ]
  • [ 144042-81-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In butan-1-ol at 65℃; for 24h;
Reference： [1]Kaiser; Spagnuolo; Adams Jr.; Audia; Dupont; Hatoum; Lowe; Prosser; Sturm; Noronha-Blob [Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4415 - 4424]
  • 5
  • [ 695-34-1 ]
  • [ 17157-48-1 ]
  • [ 874-39-5 ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 6
  • [ 33513-42-7 ]
  • [ 874-39-5 ]
  • [ 30384-94-2 ]
YieldReaction ConditionsOperation in experiment
59% With trichlorophosphate
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 7
  • [ 79-03-8 ]
  • [ 874-39-5 ]
  • 1-(7-methyl-imidazo[1,2-<i>a</i>]pyridin-3-yl)-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In toluene at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 8
  • [ 3282-30-2 ]
  • [ 874-39-5 ]
  • 2,2-dimethyl-1-(7-methyl-imidazo[1,2-<i>a</i>]pyridin-3-yl)-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In toluene at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 9
  • [ 108-24-7 ]
  • [ 874-39-5 ]
  • 1-(7-methyl-imidazo[1,2-<i>a</i>]pyridin-3-yl)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In toluene at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 10
  • [ 98-88-4 ]
  • [ 874-39-5 ]
  • [ 91427-49-5 ]
  • 7-methylimidazo[1,2-a](pyridin-3-yl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 53% In 1,4-dioxane at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 11
  • [ 98-88-4 ]
  • [ 874-39-5 ]
  • 7-methylimidazo[1,2-a](pyridin-3-yl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In toluene at 130℃; for 30h; var. acyl chlorides;
75% In toluene at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
[2]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 12
  • [ 98-88-4 ]
  • [ 874-39-5 ]
  • 1-benzoyl-7-methyl-imidazo[1,2-<i>a</i>]pyridin-1-ium; chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In tetrahydrofuran for 3h; Ambient temperature;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 13
  • [ 638-29-9 ]
  • [ 874-39-5 ]
  • 1-(7-methyl-imidazo[1,2-<i>a</i>]pyridin-3-yl)-pentan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In toluene at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 14
  • [ 75-36-5 ]
  • [ 874-39-5 ]
  • 1-(7-methyl-imidazo[1,2-<i>a</i>]pyridin-3-yl)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In toluene at 130℃; for 30h;
Reference： [1]Chayer, Said; Schmitt, Martine; Collot, Valerie; Bourguignon, Jean-Jacques [Tetrahedron Letters, 1998, vol. 39, # 52, p. 9685 - 9688]
  • 15
  • [ 695-34-1 ]
  • [ 2032-35-1 ]
  • [ 874-39-5 ]
YieldReaction ConditionsOperation in experiment
32% With sodium carbonate In 1,4-dioxane; water for 22h; Heating;
Reference： [1]Tomoda, Haruhiko; Hirano, Takafumi; Saito, Shojiro; Mutai, Toshiki; Araki, Koji [Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 6, p. 1327 - 1334]
YieldReaction ConditionsOperation in experiment
Rk. mit Elektrophilen;
Rk. mit SeO2 / Eg.;
Rk. mit Cyclohexanon, Phenyllithium -> 3-(1-Hydroxy-cyclohexyl)-7-methyl-imidazo(1,2-a)pyridin;
YieldReaction ConditionsOperation in experiment
67%
2-Amino-4-methylpyridin, Bromacetaldehyd-dimethylacetal, HBr;
aus 2-Imino-4-methyl-1-(2,2-dimethoxy-ethyl)-1,2-dihydro-pyridin durch Eintragen bei 0grad in konz. H2SO4 (90grad, 5h);
entspr. Iminoacetal;

  • 18
  • [ 874-39-5 ]
  • C16H10N4O2Se [ No CAS ]
YieldReaction ConditionsOperation in experiment
2% With selenium(IV) oxide In nitrobenzene at 210℃;
Reference： [1]Chezal; Moreau; Delmas; Gueiffier; Blache; Grassy; Lartigue; Chavignon; Teulade [Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6576 - 6584]
  • 19
  • [ 104-88-1 ]
  • [ 874-39-5 ]
  • C23H19ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium acetate; acetic acid for 24h; Heating;
Reference： [1]Zhang, Rui; Hu, Yongzhou [Synthetic Communications, 2004, vol. 34, # 21, p. 3955 - 3962]
  • 20
  • [ 100-52-7 ]
  • [ 874-39-5 ]
  • C23H20N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With sodium acetate; acetic acid for 24h; Heating;
Reference： [1]Zhang, Rui; Hu, Yongzhou [Synthetic Communications, 2004, vol. 34, # 21, p. 3955 - 3962]
  • 21
  • [ 135-02-4 ]
  • [ 874-39-5 ]
  • C24H22N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium acetate; acetic acid for 24h; Heating;
Reference： [1]Zhang, Rui; Hu, Yongzhou [Synthetic Communications, 2004, vol. 34, # 21, p. 3955 - 3962]
  • 22
  • [ 123-38-6 ]
  • [ 874-39-5 ]
  • 7-methyl-3-propenyl-imidazo[1,2-<i>a</i>]pyridine [ No CAS ]
  • 7-methyl-3-propenyl-imidazo[1,2-<i>a</i>]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid at 130℃; for 10h; Title compound not separated from byproducts;
Reference： [1]Zhang, Rui; Hu, Yongzhou [Synthetic Communications, 2007, vol. 37, # 3, p. 377 - 389]
  • 23
  • [ 78-84-2 ]
  • [ 874-39-5 ]
  • 7-methyl-3-(2-methyl-propenyl)-imidazo[1,2-<i>a</i>]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid at 130℃; for 10h;
Reference： [1]Zhang, Rui; Hu, Yongzhou [Synthetic Communications, 2007, vol. 37, # 3, p. 377 - 389]
  • 24
  • [ 874-39-5 ]
  • 2-methyl-1-(7-methyl-imidazo[1,2-<i>a</i>]pyridin-3-yl)-propane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / acetic acid / 10 h / 130 °C 2: 52 percent / hydrogen peroxide; formic acid / 40 °C
Reference： [1]Zhang, Rui; Hu, Yongzhou [Synthetic Communications, 2007, vol. 37, # 3, p. 377 - 389]
  • 25
  • [ 874-39-5 ]
  • [ 29096-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 26
  • [ 874-39-5 ]
  • [ 1019023-64-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 27
  • [ 874-39-5 ]
  • 3-Ethylsulfanylmethyl-7-methyl-imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating 4: pyridine / acetonitrile / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 28
  • [ 874-39-5 ]
  • 1-(7-Methyl-imidazo[1,2-a]pyridin-3-ylmethylsulfanyl)-propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating 4: pyridine / acetonitrile / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 29
  • [ 874-39-5 ]
  • 3-(7-Methyl-imidazo[1,2-a]pyridin-3-ylmethylsulfanyl)-propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating 4: pyridine / acetonitrile / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 30
  • [ 874-39-5 ]
  • 3-(7-Methyl-imidazo[1,2-a]pyridin-3-ylmethylsulfanyl)-propane-1,2-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating 4: pyridine / acetonitrile / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 31
  • [ 874-39-5 ]
  • 3-Benzylsulfanylmethyl-7-methyl-imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating 4: pyridine / acetonitrile / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 32
  • [ 874-39-5 ]
  • (7-Methyl-imidazo[1,2-a]pyridin-3-ylmethylsulfanyl)-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 59 percent / POCl3 2: 91 percent / NaBH4 / methanol 3: SOCl2 / Heating 4: pyridine / acetonitrile / Heating
Reference： [1]Gueiffier, Alain; Lhassani, Mohammed; Elhakmaoui, Ahmed; Snoeck, Robert; Andrei, Graciela; Chavignon, Olivier; Teulade, Jean-Claude; Kerbal, Abdelali; Essassi, El Mokhtar; Debouzy, Jean-Claude; Witvrouw, Myriam; Blache, Yves; Balzarini, Jan; De Clercq, Erik; Chapat, Jean-Pierre [Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859]
  • 33
  • [ 874-39-5 ]
  • [ 648423-85-2 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; oxygen In 1,2-dimethoxyethane at 70℃; for 96h; 8 [1152] To a 50 ml capacity high-pressure reactor containing 7-methylimidazo[1,2-a]pyridine (1.0 g, 6.7 mmol), KOH (5.1 g, 90.7 mmol), and 18-crown-6 (0.3 g, 1.2 mmol) is added DME (15 ml). The mixture is stirred at 70° C. and 150 psi of O2 for 4 days. The reaction mixture is diluted with H2O (15 ml) and extracted with CH2Cl2 (3×40 ml). The aqueous layer is acidified with conc. HCl and the solvent is removed under vacuum. The KCl salt crystallized out of the mixture from H2O/EtOH/Et2O. The filtrate is concentrated to give a brown solid (1.2 g) for imidazo[1,2-a]pyridine-6-carboxylic acid. This compound is used without further purification. HRMS (FAB) calcd for C8H6N2O2+H 163.0508, found 163.0491.
Reference： [1]Current Patent Assignee: PFIZER INC - US2003/236264, 2003, A1 Location in patent: Page 52
  • 34
  • [ 874-39-5 ]
  • [ 59938-33-9 ]
YieldReaction ConditionsOperation in experiment
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 2h; AA.2 Procedure AA2 -lodination; To a solution of 7-substituted lmidazo[1 ,2-a]pyridine (1.0 equiv) in DMF was added N- iodosuccinimide (1.2 equiv) and the resulting mixture was stirred for 2 h at room temperature. The thin brown slurry was diluted with water, 10%w/v sodium thiosulfate and sodium carbonate (1M) and extracted with CH2Ck- The aqueous was further extracted with CH2CI2. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo to give the product. Where necessary, the product was further purified by trituration or column chromatography on silica.
With N-iodo-succinimide In acetonitrile
Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2008/78100, 2008, A2 Location in patent: Page/Page column 125-126
[2]Juillet, Charlotte; Ermolenko, Ludmila; Boyarskaya, Dina; Baratte, Blandine; Josselin, Béatrice; Nedev, Hristo; Bach, Stéphane; Iorga, Bogdan I.; Bignon, Jérôme; Ruchaud, Sandrine; Al-Mourabit, Ali [Journal of Medicinal Chemistry, 2021, vol. 64, # 2, p. 1197 - 1219]
  • 35
  • [ 874-39-5 ]
  • [ 1490-25-1 ]
  • [ 430440-70-3 ]
YieldReaction ConditionsOperation in experiment
12% Stage #1: 7-Methyl-imidazo[1,2-a]pyridine With aluminum (III) chloride In carbon disulfide at 0℃; for 0.5h; Stage #2: succinic acid monomethylester chloride In carbon disulfide for 2h; Heating / reflux; A.2 7-methylimidazo[1,2-a]pyridine (0.50 g, 3.62 mmol) is dissolved in CS2 (8 mL). The solution is cooled to 0° C., and aluminum chloride (1.40 g, 5.35 mmol) is added in small portions. It is stirred for 30 min, and then the reaction medium is brought to reflux. An acid chloride (1.50 g, 10 mmol) is added, and it is stirred at reflux for 2 h. The solution is cooled and pouredice. The pH is adjusted to 9 by addition of 3N NaOH. It is extracted with ethyl acetate and then filtered using diatomaceous earth. The ethyl acetate phase is dried using sodium sulfate and then evaporated to dryness. Finally, it is triturated with ether, and the product obtained is filtered. light-maroon powder MM(C13H14N2O3): 246.26 g mass: 100 g Yield: 12% {circle(1)}RMN(1, 300 MHz, CDCl3): 9, 50(d, 1H, CHarom., J3 =6, 7 Hz); 8, 40(s, 1H, CHimidaz.); 7, 50(s, 1H, CHarom.); 6, 91(d, 1H, CHarom., J3 = 6, 7 Hz); 3, 75(s, 3H, -CH3); 3, 28(t, 2H, -CH2-, J3 =6, 7 Hz); 2, 81(t, 2H, -CH2-, J3 = 6, 7 Hz); 2, 50 (s, 3H, -CH3).
Reference： [1]Current Patent Assignee: UNIVERSITY OF STRASBOURG - US2005/113366, 2005, A1 Location in patent: Page/Page column 5-6
  • 36
  • [ 874-39-5 ]
  • [ 71-43-2 ]
  • [ 882187-78-2 ]
YieldReaction ConditionsOperation in experiment
79% With oxygen; palladium diacetate; silver carbonate; Trimethylacetic acid In N,N-dimethyl-formamide at 130℃; for 20h; regioselective reaction; General procedure: imidazo[1,2-a]pyridine 1a (118mg, 1 mmol), benzene ( 2a, 1 mL), Pd(OAc)2 (5 mol%), Ag2CO3(5 mol%) and PivOH (1.2 eq) were stirred in DMF (2 mL) at 130 °C equipped with oxygen bag for 20 h. After completion of the reaction (monitored by TLC),the water (10mL) was added. The aqueous solution was extracted with ethyl acetate (3×15 mL) and the combined extract was dried with anhydrous MgSO4.The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether : ethyl acetate=21) to give a pure sample of 3a (Yellowoil, 144 mg, yield 74%).
Reference： [1]Wang, Shaohua; Liu, Wenjie; Cen, Jinghe; Liao, Jinqiang; Huang, Jianping; Zhan, Haiying [Tetrahedron Letters, 2014, vol. 55, # 9, p. 1589 - 1592]
  • 37
  • [ 108-38-3 ]
  • [ 874-39-5 ]
  • [ 1560900-19-7 ]
YieldReaction ConditionsOperation in experiment
73% With oxygen; palladium diacetate; silver carbonate; Trimethylacetic acid In N,N-dimethyl-formamide at 130℃; for 20h; regioselective reaction; General procedure: imidazo[1,2-a]pyridine 1a (118mg, 1 mmol), benzene ( 2a, 1 mL), Pd(OAc)2 (5 mol%), Ag2CO3(5 mol%) and PivOH (1.2 eq) were stirred in DMF (2 mL) at 130 °C equipped with oxygen bag for 20 h. After completion of the reaction (monitored by TLC),the water (10mL) was added. The aqueous solution was extracted with ethyl acetate (3×15 mL) and the combined extract was dried with anhydrous MgSO4.The solvent was removed and the crude product was separated by column chromatography (eluted with petroleum ether : ethyl acetate=21) to give a pure sample of 3a (Yellowoil, 144 mg, yield 74%).
Reference： [1]Wang, Shaohua; Liu, Wenjie; Cen, Jinghe; Liao, Jinqiang; Huang, Jianping; Zhan, Haiying [Tetrahedron Letters, 2014, vol. 55, # 9, p. 1589 - 1592]
  • 38
  • [ 874-39-5 ]
  • [ 140-88-5 ]
  • [ 1642164-58-6 ]
YieldReaction ConditionsOperation in experiment
70% With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 120℃; for 24h; stereoselective reaction;
Reference： [1]Zhan, Haiying; Zhao, Limin; Li, Naiying; Chen, Longbin; Liu, Jingyun; Liao, Jinqiang; Cao, Hua [RSC Advances, 2014, vol. 4, # 60, p. 32013 - 32016]
  • 39
  • [ 292638-85-8 ]
  • [ 874-39-5 ]
  • [ 1642164-57-5 ]
YieldReaction ConditionsOperation in experiment
72% With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 120℃; for 24h; stereoselective reaction;
Reference： [1]Zhan, Haiying; Zhao, Limin; Li, Naiying; Chen, Longbin; Liu, Jingyun; Liao, Jinqiang; Cao, Hua [RSC Advances, 2014, vol. 4, # 60, p. 32013 - 32016]
  • 40
  • [ 874-39-5 ]
  • [ 172975-69-8 ]
  • [ 1560900-19-7 ]
YieldReaction ConditionsOperation in experiment
80% With oxygen; copper diacetate; palladium diacetate In 1,4-dioxane at 120℃; regioselective reaction;
Reference： [1]Zhao, Limin; Zhan, Haiying; Liao, Jinqiang; Huang, Jianping; Chen, Qinlin; Qiu, Huifang; Cao, Hua [Catalysis Communications, 2014, vol. 56, p. 65 - 67]
  • 41
  • [ 874-39-5 ]
  • [ 98-80-6 ]
  • [ 882187-78-2 ]
YieldReaction ConditionsOperation in experiment
78% With oxygen; copper diacetate; palladium diacetate In 1,4-dioxane at 120℃; regioselective reaction;
Reference： [1]Zhao, Limin; Zhan, Haiying; Liao, Jinqiang; Huang, Jianping; Chen, Qinlin; Qiu, Huifang; Cao, Hua [Catalysis Communications, 2014, vol. 56, p. 65 - 67]
  • 42
  • [ 100-42-5 ]
  • [ 874-39-5 ]
  • C16H14N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With oxygen; palladium diacetate; acetic anhydride; acetic acid; silver carbonate In 1,4-dioxane at 120℃; for 24h; regioselective reaction;
Reference： [1]Cao, Hua; Lei, Sai; Liao, Jinqiang; Huang, Jianping; Qiu, Huifang; Chen, Qinlin; Qiu, Shuxian; Chen, Yaoyi [RSC Advances, 2014, vol. 4, # 91, p. 50137 - 50140]
  • 43
  • [ 405-99-2 ]
  • [ 874-39-5 ]
  • C16H13FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With oxygen; palladium diacetate; acetic anhydride; acetic acid; silver carbonate In 1,4-dioxane at 120℃; for 24h; regioselective reaction;
Reference： [1]Cao, Hua; Lei, Sai; Liao, Jinqiang; Huang, Jianping; Qiu, Huifang; Chen, Qinlin; Qiu, Shuxian; Chen, Yaoyi [RSC Advances, 2014, vol. 4, # 91, p. 50137 - 50140]
  • 44
  • [ 1746-23-2 ]
  • [ 874-39-5 ]
  • C20H22N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With oxygen; palladium diacetate; acetic anhydride; acetic acid; silver carbonate In 1,4-dioxane at 120℃; for 24h; regioselective reaction;
Reference： [1]Cao, Hua; Lei, Sai; Liao, Jinqiang; Huang, Jianping; Qiu, Huifang; Chen, Qinlin; Qiu, Shuxian; Chen, Yaoyi [RSC Advances, 2014, vol. 4, # 91, p. 50137 - 50140]
  • 45
  • [ 1746-23-2 ]
  • [ 874-39-5 ]
  • C16H13ClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With oxygen; palladium diacetate; acetic anhydride; acetic acid; silver carbonate In 1,4-dioxane at 120℃; for 24h; regioselective reaction;
Reference： [1]Cao, Hua; Lei, Sai; Liao, Jinqiang; Huang, Jianping; Qiu, Huifang; Chen, Qinlin; Qiu, Shuxian; Chen, Yaoyi [RSC Advances, 2014, vol. 4, # 91, p. 50137 - 50140]
  • 46
  • [ 292638-85-8 ]
  • [ 874-39-5 ]
  • C12H12N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With oxygen; palladium diacetate; acetic anhydride; acetic acid; silver carbonate In 1,4-dioxane at 120℃; for 24h; regioselective reaction;
Reference： [1]Cao, Hua; Lei, Sai; Liao, Jinqiang; Huang, Jianping; Qiu, Huifang; Chen, Qinlin; Qiu, Shuxian; Chen, Yaoyi [RSC Advances, 2014, vol. 4, # 91, p. 50137 - 50140]
  • 47
  • [ 874-39-5 ]
  • [ 140-88-5 ]
  • C13H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With oxygen; palladium diacetate; acetic anhydride; acetic acid; silver carbonate In 1,4-dioxane at 120℃; for 24h; regioselective reaction;
Reference： [1]Cao, Hua; Lei, Sai; Liao, Jinqiang; Huang, Jianping; Qiu, Huifang; Chen, Qinlin; Qiu, Shuxian; Chen, Yaoyi [RSC Advances, 2014, vol. 4, # 91, p. 50137 - 50140]
  • 48
  • [ 67-68-5 ]
  • [ 874-39-5 ]
  • [ 30384-94-2 ]
YieldReaction ConditionsOperation in experiment
85% With iron(III) chloride; oxygen; acetic acid at 100℃; for 12h; chemoselective reaction; Typical procedure for aerobic iron(III)-catalyzed direct formylation of imidazo[1,2-a]pyridine to form 3-formylimidazo[1,2-a]pyridine General procedure: FeCl3 (0.025 mmol, 4 mg) and AcOH (0.1 mmol, 6 mg) was mixed with DMSO (3 mL) in a glass vial or round-bottom flask equipped with a magnetic stirring bar. Then, substrate 1 (0.5 mmol) was added. The mixture was stirred under an dioxygen atmosphere (1 atm) at 100°C for 12 h. After cooling down to room temperature, 5 mL of ethyl acetate was added and removal of the DMSO with brine, the residue was purified by flash chromatography on silica gel to obtain the desired product 2 using light petroleum ether/ethyl acetate (4:1, v/v) as eluent, which furnished the 3-formylimidazo[1,2-a]pyridine.
83% With oxygen; copper diacetate; acetic acid at 120℃; for 24h;
Reference： [1]Xiang, Shijian; Chen, Huoji; Liu, Qiang [Tetrahedron Letters, 2016, vol. 57, # 34, p. 3870 - 3872]
[2]Cao, Hua; Lei, Sai; Li, Naiying; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Qiu, Shuxian; Tan, Jingwen [Chemical Communications, 2015, vol. 51, # 10, p. 1823 - 1825]
  • 49
  • [ 149-30-4 ]
  • [ 874-39-5 ]
  • C15H11N3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With oxygen; copper diacetate In N,N-dimethyl acetamide at 80℃; regioselective reaction;
Reference： [1]Zheng, Zhishuo; Qi, Deyu; Shi, Lei [Catalysis Communications, 2015, vol. 66, p. 83 - 86]
  • 50
  • [ 371-42-6 ]
  • [ 874-39-5 ]
  • C14H11FN2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With oxygen; copper diacetate In N,N-dimethyl acetamide at 80℃; regioselective reaction;
Reference： [1]Zheng, Zhishuo; Qi, Deyu; Shi, Lei [Catalysis Communications, 2015, vol. 66, p. 83 - 86]
  • 51
  • [ 7217-59-6 ]
  • [ 874-39-5 ]
  • C15H14N2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With oxygen; copper diacetate In N,N-dimethyl acetamide at 80℃; regioselective reaction;
Reference： [1]Zheng, Zhishuo; Qi, Deyu; Shi, Lei [Catalysis Communications, 2015, vol. 66, p. 83 - 86]
  • 52
  • [ 1569-69-3 ]
  • [ 874-39-5 ]
  • C14H18N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;
Reference： [1]Cao, Hua; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Deng, Hao; Chen, Guijun; Yan, Caijuan; Chen, Ya [RSC Advances, 2015, vol. 5, # 29, p. 22356 - 22360]
  • 53
  • [ 874-39-5 ]
  • [ 112-55-0 ]
  • C20H32N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;
Reference： [1]Cao, Hua; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Deng, Hao; Chen, Guijun; Yan, Caijuan; Chen, Ya [RSC Advances, 2015, vol. 5, # 29, p. 22356 - 22360]
  • 54
  • [ 109-79-5 ]
  • [ 874-39-5 ]
  • C12H16N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;
Reference： [1]Cao, Hua; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Deng, Hao; Chen, Guijun; Yan, Caijuan; Chen, Ya [RSC Advances, 2015, vol. 5, # 29, p. 22356 - 22360]
  • 55
  • [ 874-39-5 ]
  • [ 75-08-1 ]
  • C10H12N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;
Reference： [1]Cao, Hua; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Deng, Hao; Chen, Guijun; Yan, Caijuan; Chen, Ya [RSC Advances, 2015, vol. 5, # 29, p. 22356 - 22360]
  • 56
  • [ 100-53-8 ]
  • [ 874-39-5 ]
  • C15H14N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;
Reference： [1]Cao, Hua; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Deng, Hao; Chen, Guijun; Yan, Caijuan; Chen, Ya [RSC Advances, 2015, vol. 5, # 29, p. 22356 - 22360]
  • 57
  • [ 874-39-5 ]
  • 7-methyl-3-(7-methyl-imidazo[1,2-a]pyridin-3-yl)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; regioselective reaction;
Reference： [1]Lei, Sai; Cao, Hua; Chen, Longbin; Liu, Jingyun; Cai, Huiyin; Tan, Jingwen [Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3109 - 3114]
  • 58
  • [ 127-19-5 ]
  • [ 874-39-5 ]
  • N,N-dimethyl-2-(7-methylimidazo[1,2-a]pyridin-3-yl)-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tert-Amyl alcohol; oxygen; copper diacetate; acetic acid In N,N-dimethyl acetamide at 120℃; for 24h; regioselective reaction;
Reference： [1]Wang, Changcheng; Lei, Sai; Cao, Hua; Qiu, Shuxian; Liu, Jingyun; Deng, Hao; Yan, Caijuan [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12725 - 12732]
  • 59
  • [ 874-39-5 ]
  • [ 67-64-1 ]
  • 1-(7-methylimidazo[1,2-a]pyridin-3-yl)propane-1,2-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tert-Amyl alcohol; oxygen; copper diacetate; acetic acid In 1,2-dichloro-ethane at 120℃; for 24h; Sealed tube; regioselective reaction;
Reference： [1]Wang, Changcheng; Lei, Sai; Cao, Hua; Qiu, Shuxian; Liu, Jingyun; Deng, Hao; Yan, Caijuan [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12725 - 12732]
  • 60
  • [ 98-86-2 ]
  • [ 874-39-5 ]
  • 1-(7-methylimidazo[1,2-a]pyridin-3-yl)-2-phenylethane-1,2-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With oxygen; copper diacetate; acetic acid In toluene at 140℃; for 12h; Schlenk technique; Sealed tube; regioselective reaction;
Reference： [1]Lei, Sai; Chen, Guijun; Mai, Yingying; Chen, Longbin; Cai, Huiyin; Tan, Jingwen; Cao, Hua [Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 67 - 73]
  • 61
  • [ 109-06-8 ]
  • [ 874-39-5 ]
  • (7-methylimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With oxygen; copper diacetate; trifluoroacetic acid In toluene at 130℃; Schlenk technique; Sealed tube; regioselective reaction;
Reference： [1]Lei, Sai; Mai, Yingying; Yan, Caijuan; Mao, Jianwen; Cao, Hua [Organic Letters, 2016, vol. 18, # 15, p. 3582 - 3585]
  • 62
  • [ 89-98-5 ]
  • [ 874-39-5 ]
  • 4-methyl-6H-benzol[b]imidazo[5,1,2-de]quinolizin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl acetamide; water at 140℃; for 24h;
90% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl acetamide; water at 140℃; for 24h; 34 In a 10 ml flask,Add the magnet,7-Methylimidazo [1,2-a] pyridine (0.3 mmol) was added,2-chlorobenzaldehyde (0.9 mmol),Potassium carbonate (0.9 mmol),Tetrabutylammonium bromide (0.9 mmol),Palladium acetate (5 mol%),4,5-bis (diphenylphosphino) -9,9-dimethylXanthene (10mol%),N, N-dimethylacetamide (4 mL),Water (0.1 mL).The reaction mixture was reacted in a 140 ° oil bath for 24 hours,Cooled to room temperature,An appropriate amount of water was added and extracted three times with ethyl acetate,Combine organic phase,Dried over anhydrous magnesium sulfate, concentrated by filtration,Concentrated column chromatography,The product was isolated 63 mg,Yield 90%.
Reference： [1]Mu, Bing; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Chang, Junbiao; Wu, Yangjie [Organic Letters, 2016, vol. 18, # 20, p. 5260 - 5263]
[2]Current Patent Assignee: UNIV ZHENGZHOU NORMAL; ZHENGZHOU UNIVERSITY - CN106279168, 2017, A Location in patent: Paragraph 0152; 0153; 0154; 0155; 0156
  • 63
  • [ 108-41-8 ]
  • [ 874-39-5 ]
  • C15H14N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Inert atmosphere;
Reference： [1]Liu, Qing-Xian; He, Bang-Yue; Qian, Peng-Cheng; Shao, Li-Xiong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1151 - 1154]
  • 64
  • [ 348-51-6 ]
  • [ 874-39-5 ]
  • C14H11FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Inert atmosphere;
Reference： [1]Liu, Qing-Xian; He, Bang-Yue; Qian, Peng-Cheng; Shao, Li-Xiong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1151 - 1154]
  • 65
  • [ 352-33-0 ]
  • [ 874-39-5 ]
  • 3-(4-fluorophenyl)-7-methylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Inert atmosphere;
Reference： [1]Liu, Qing-Xian; He, Bang-Yue; Qian, Peng-Cheng; Shao, Li-Xiong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1151 - 1154]
  • 66
  • [ 108-90-7 ]
  • [ 874-39-5 ]
  • [ 882187-78-2 ]
YieldReaction ConditionsOperation in experiment
94% With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Inert atmosphere;
94% With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; 1 Table 3. Nitrogen heterocyclic carbene-palladium complex 4 catalyzes the reaction of 1 and 2. A Unless otherwise specified, all reactions were carried out in 1 (0.5 mmol), 2 (0.75 mmol), 4 (2.0 mol%), NaOtBu(3.0 equiv.), Tetrahydrofuran (0.5 mL) was reacted at 120 ° C for 12 hours. B separation yield. C130 .
Reference： [1]Liu, Qing-Xian; He, Bang-Yue; Qian, Peng-Cheng; Shao, Li-Xiong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1151 - 1154]
[2]Current Patent Assignee: WENZHOU UNIVERSITY - CN106565704, 2017, A Location in patent: Paragraph 0043; 0044; 0045; 0046
  • 67
  • [ 2845-89-8 ]
  • [ 874-39-5 ]
  • [ 342613-56-3 ]
YieldReaction ConditionsOperation in experiment
88% With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Inert atmosphere;
Reference： [1]Liu, Qing-Xian; He, Bang-Yue; Qian, Peng-Cheng; Shao, Li-Xiong [Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1151 - 1154]
  • 68
  • [ 874-39-5 ]
  • [ 93-61-8 ]
  • [ 30384-94-2 ]
YieldReaction ConditionsOperation in experiment
98.8% With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In ethanol at 80℃; for 11h; 4 To the dry reaction vessel was added an appropriate amount of organic solvent ethanol, and then 100 mmol of the compound of formula (II), 150 mmol of compound of formula (III), 5 mmol of copper trifluoroacetylacetonate, 200 mmol of TBHP and 6 mmol of reaction aid (5 mmol Butylpyridine p-toluenesulfonate and 1 mmol of cyclooctatetriene tetracarbonyl iron) was added elevated temperature to 80 ° C and reacted at that temperature for 11 hours.After completion of the reaction, the mixture was allowed to cool to room temperature, and then the saturated aqueous solution of sodium bicarbonate was sufficiently washed. The organic phase was separated, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was separated by silica gel column chromatography (column chromatography The mixture was a mixture of ethyl acetate and n-propanol, and the volume ratio of the two was 10: 2) to give the compound of formula (I) in a yield of 98.8%.
Reference： [1]Current Patent Assignee: HUNAN EXPERSON CHEMICAL TECHNOLOGY CO., LTD; YANG, HUA; QING, GUANGZONG; YU, XING - CN104592225, 2016, B Location in patent: Paragraph 0050- 0053
  • 69
  • [ 766-85-8 ]
  • [ 874-39-5 ]
  • [ 342613-56-3 ]
YieldReaction ConditionsOperation in experiment
82% With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; General procedure for the direct arylation on water 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]Kalari, Saradhi; Babar, Dattatraya A.; Karale, Uttam B.; Makane, Vitthal B.; Rode, Haridas B. [Tetrahedron Letters, 2017, vol. 58, # 29, p. 2818 - 2821]
  • 70
  • [ 352-34-1 ]
  • [ 874-39-5 ]
  • 3-(4-fluorophenyl)-7-methylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; General procedure for the direct arylation on water 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]Kalari, Saradhi; Babar, Dattatraya A.; Karale, Uttam B.; Makane, Vitthal B.; Rode, Haridas B. [Tetrahedron Letters, 2017, vol. 58, # 29, p. 2818 - 2821]
  • 71
  • [ 874-39-5 ]
  • [ 56051-32-2 ]
YieldReaction ConditionsOperation in experiment
72% With sodium bromite; acetic acid In N,N-dimethyl-formamide at 60℃; for 10h; regioselective reaction;
Reference： [1]Li, Junxuan; Tang, Jiayi; Wu, Yuanheng; He, Qiuxing; Yu, Yue [RSC Advances, 2018, vol. 8, # 9, p. 5058 - 5062]
  • 72
  • [ 874-39-5 ]
  • [ 59938-28-2 ]
YieldReaction ConditionsOperation in experiment
85% With sodium chlorite; acetic acid In N,N-dimethyl-formamide at 60℃; for 10h; regioselective reaction;
Reference： [1]Li, Junxuan; Tang, Jiayi; Wu, Yuanheng; He, Qiuxing; Yu, Yue [RSC Advances, 2018, vol. 8, # 9, p. 5058 - 5062]
  • 73
  • [ 591-50-4 ]
  • [ 874-39-5 ]
  • [ 882187-78-2 ]
YieldReaction ConditionsOperation in experiment
86% With cobalt(II) chloride hexahydrate; potassium acetate In N,N-dimethyl-formamide at 150℃; for 24h;
Reference： [1]Babar, Dattatraya A.; Rode, Haridas B. [European Journal of Organic Chemistry, 2020, vol. 2020, # 12, p. 1823 - 1827]
  • 74
  • [ 624-31-7 ]
  • [ 874-39-5 ]
  • 7-methyl-3-(p-tolyl)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With cobalt(II) chloride hexahydrate; potassium acetate In N,N-dimethyl-formamide at 150℃; for 24h;
Reference： [1]Babar, Dattatraya A.; Rode, Haridas B. [European Journal of Organic Chemistry, 2020, vol. 2020, # 12, p. 1823 - 1827]
  • 75
  • S-phenethyl thiosulfate O-sodium salt [ No CAS ]
  • [ 874-39-5 ]
  • 7-methyl-3-(phenethylthio)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With iodine In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; General procedure D: The coupling of Bunte salts to imidazo[1,2-a]pyridines General procedure: To a flame dried Schlenk tube with a magnetic stirring bar was added imidazo[1,2-a]pyridine(1 equiv), the appropriate Bunte salt (1.5 equiv) and iodine (20 mol%). The tube was sealedwith a rubber septum, and placed under an atmosphere of argon, followed by the additionof DMSO via syringe (0.15 M). The septum was replaced by a Teflon screw cap under argon flow. The reaction mixture was stirred at 80 C for 24 h. After cooling to room temperature,a saturated solution of Na2S2O3 was added and the product extracted with EtOAc. Thecombined organic layers was washed with H2O and brine, dried over MgSO4, filtered andthen concentrated in vacuo. Purification by recrystallisation from pentane or by flashchromatography over silica gel, eluting with a gradient of petroleum ether to 30% ethylacetate/petroleum ether afforded the corresponding sulfides.
Reference： [1]Al-Saedy, Muhannad A. E.; Harrity, Joseph P. A. [Synlett, 2020, vol. 31, # 12, p. 1182 - 1184]
  • 76
  • [ 874-39-5 ]
  • 4,5-dibromo-N-(3-(7-methylimidazo[1,2-a]pyridin-3-yl)prop-2-yn-1-yl)-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / Inert atmosphere
Reference： [1]Juillet, Charlotte; Ermolenko, Ludmila; Boyarskaya, Dina; Baratte, Blandine; Josselin, Béatrice; Nedev, Hristo; Bach, Stéphane; Iorga, Bogdan I.; Bignon, Jérôme; Ruchaud, Sandrine; Al-Mourabit, Ali [Journal of Medicinal Chemistry, 2021, vol. 64, # 2, p. 1197 - 1219]

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