Methyl imidazo(1,2-a)pyridine-6-carboxylate → Methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate
Reaction equation
[I:1]NC(=O)CCC(N)=O.[CH3:10][O:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[CH:21][N:22]=2)[CH:19]=1)=[O:13]>C(#N)C>[CH3:10][O:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([I:1])=[CH:21][N:22]=2)[CH:19]=1)=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-iodosuccinamide (1.55 g, 6.89 mmol) was added to a solution of imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (1.1 g, 6.24 mmol) in acetonitrile (50 mL) which had been cooled to 0° C. under a nitrogen atmosphere. The reaction stirred for 1 hr, then concentrated in vaccuo to a residue. The residue was dissolved in ethyl acetate (50 mL) and washed with 10% sodium bisulfate (2×10 ml) and brine (1×20 mL), then the organic layers were dried over MgSO4 and evaporated to give 3-iodo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester as a pale yellow solid (1.79 g, 95%). 1H NMR (250 MHz, CDCl3): δ 8.91 (s, 1H), 7.85 (dd, 1H, J=2.5, J=10), 7.80 (s, 1H), 7.69 (d, 1H, J=10), 4.01 (s, 3H).
Workup
- concentrationconcentrated in vaccuo to a residue
- dissolutionThe residue was dissolved in ethyl acetate (50 mL)
- washwashed with 10% sodium bisulfate (2×10 ml) and brine (1×20 mL)
- dry with materialthe organic layers were dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-5e49c718ddbe42b087c700108fb1ba47
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348359B2
Reaction notes
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