Ethyl bromopyruvate → Ethyl 6-iodoimidazo[1,2-a]pyridine-2-carboxylate

HRID 751270Notes

Reaction equation

HRID 751270 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5](=O)[CH2:6]Br)[CH3:2].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][N:12]=1>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[N:10]=[C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][N:12]2[CH:6]=1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 3681971Ethyl 6-iodoimidazo[1,2-a]pyridine-2-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 3-bromo-2-oxo-propionic acid ethyl ester (1.75 g, 9.09 mmol) to a solution of 2-amino-5-iodo pyridine (Tetrahedron 2002, 58, 2885-2890; 1.0 g, 4.54 mmol) in acetonitrile (100 ml). Reflux for 12 h, concentrate to ˜30 ml, and dilute with saturated aqueous sodium bicarbonate. Extract into dichloromethane, combine organic extracts, dry over anhydrous magnesium sulfate, and concentrate. Titurate the residue in diethyl ether and filter to give 0.8 g (56%) of the subtitled compound as an off-white solid. TOF MS ES+ exact mass calculated for C10H91N2O2 (p+1): m/z=316.9787; Found: 316.9784. 1H NMR (400 MHz, DMSO-d6) δ 8.97 (m, 1H), 8.46 (s, 1H), 7.57-7.49 (m, 2H), 4.32 (q, T 7.0 Hz, 2 Hz), 1.33 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureReflux for 12 h
  2. concentrationconcentrate to ˜30 ml
  3. additiondilute with saturated aqueous sodium bicarbonate
  4. extractionExtract into dichloromethane
  5. dry with materialdry over anhydrous magnesium sulfate
  6. concentrationconcentrate
  7. filtrationfilter

Sources & evidence

ORD record
ord-55a7ccb448ce4cd28c80bd50a6759038
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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