Trifluoroacetic anhydride → 2-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridine
Reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5](=[N:14]S(C2C=CC(C)=CC=2)(=O)=O)[N:6]([CH:8]([C:10](=O)[CH2:11][CH3:12])[CH3:9])[CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH2:11]([C:10]1[N:14]=[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]2[C:8]=1[CH3:9])[CH3:12]Participants
4
Procedure
To a stirred solution of N-(5-iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (4 g) in THF (50 ml) was added trifluoroacetic anhydride (10 ml) at 0° C., and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, poured into saturated aqueous NaHCO3 solution and extracted with DCM. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to afford the title compound (1.3 g) as a yellow solid.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionpoured into saturated aqueous NaHCO3 solution
- extractionextracted with DCM
- washThe extract was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- custompurified by silica gel column chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-6432f6fd9d8748f19642b869821a16d5
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365540B2
Reaction notes
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