IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE
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IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE
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CAS No:
6188-43-8
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Formula:
C8H6N2O
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Chemical Name:
IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE
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Synonyms:
[1,2-α]PYRIDIN-3-CARBOXALDEHYDE;Imidazo[1,2-a]pyridine-3-carbaldehyde;imidazo[3,2-a]pyridine-3-carbaldehyde;3-imidazo[3,2-a]pyridinecarboxaldehyde;IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE;IMIDAZO[1,2-A]PYRIDINE-3-CARBOXALDEHYDE;Imidazo[1,2-a]pyridine-3-carbaldehyde AldrichCPR
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CAS No:
Safety Information
IRRITANT
NONH for all modes of transport
22
Xn
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory.
IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE Use and Manufacturing
To DMF (120 mL, 1.55 mol) at 2 °C, freshly distilled phosphorus oxychloride (61 mL, 0.65 mol) was slowly added. The temperature was allowed to rise gradually to room temperature. The solution was cooled again to 2 °C and a solution of imidazo[1, 2-a]-pyridine 1 (10 g, 0.085 mol) in DMF (60 mL) was added dropwise. The mixture was warmed to 105 °C, whereupon the temperature rose to 140 °C. The oil bath was removed until the temperature stabilized at 120 °C. The reaction mixture was heated for 45 min at 120 °C and 2.5 h at 85 °C, then cooled and poured into 5percent HCl (600 mL) ice-cooled and brought to pH 9 using 20percent NaOH. The resulting solution was extracted with CHa) Imidazo [1, 2-a] pyridine-3-carbaldehyde; Imidazo [1, 2-a] pyridine (0.500 g, 4.23 mmol) was dissolved in 1 mL of DMF and phosphorus oxychloride (0.71 g, 4.6 mmol) was added dropwise and the mixture was stirred and checked on LC-MS. After lh the mixture was poured into water and made alkaline with 1M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel with DCM: MeOH 99: 1-96: 4. Yield: 83 mg (13percent). 'H NMR (300 MHz, CDCl3) 6 9.95 (s, 1H), 9.50 (m, 1H), 8.32 (s, 1H), 7.80 (m, 1H), 7.56 (m, 1H), 7.13 (m, 1H).FeCl
Computed Properties
Molecular Weight:146.15
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:146.048012819
Monoisotopic Mass:146.048012819
Topological Polar Surface Area:34.4
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE
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