2-Amino-5-cyanopyridine → Ethyl 2-(6-cyanoimidazo[1,2-a]pyridin-3-yl)acetate

HRID 402892Notes

Reaction equation

HRID 402892 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH2:10]([O:12][C:13](=[O:18])/[CH:14]=[CH:15]/[CH:16]=O)[CH3:11]>C(#N)C>[CH2:10]([O:12][C:13](=[O:18])[CH2:14][C:15]1[N:3]2[CH:4]=[C:5]([C:8]#[N:9])[CH:6]=[CH:7][C:2]2=[N:1][CH:16]=1)[CH3:11]

Participants

4

Reactant 2

HCID 8182602-Amino-5-cyanopyridineHCID 7019541Ethyl (2E)-4-oxo-2-butenoate

Product 1

HCID 59192043Ethyl 2-(6-cyanoimidazo[1,2-a]pyridin-3-yl)acetateYield 30.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

2-Amino-5-cyanopyridine (5.0 g, 39.9 mmol) and ethyl-(E)-4-oxobutenoate (5.92 g, 43.9 mmol, 1.1 equiv) are dissolved in acetonitrile (25 ml). The solution is heated for 14 hours at 90° C. After cooling, volatiles are removed in vacuo, and the residue is purified by flash chromatography (gradient hexane/EtOAc 100:0 to 50:50) to afford the title compound (2.77 g, 29%). 1H NMR (400 MHz, d6-DMSO): δ=9.17-9.15 (m, 1H), 7.60 (dd, J=9.3/1.0 Hz, 1H), 7.54 (s, 1H), 7.37 (dd, J=9.3/1.7 Hz, 1H), 4.07 (s, 2H), 3.99 (q, J=7.4 Hz, 2H), 1.07 (t, J=7.1 Hz, 3H). MS (ES+): 230 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customvolatiles are removed in vacuo
  3. customthe residue is purified by flash chromatography (gradient hexane/EtOAc 100:0 to 50:50)

Sources & evidence

ORD record
ord-23b6c46a9ca447eb98bc974c24516b89
Source dataset
uspto-grants-2014_06
Patent number
US08742132B2

Reaction notes

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