Trifluoroacetic anhydride → 2-Cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine

HRID 60382Notes

Reaction equation

HRID 60382 reaction equation
[CH:1]1([C:4](=O)[CH:5]([N:7]2[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:8]2=[N:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH3:6])[CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH:1]1([C:4]2[N:14]=[C:8]3[CH:9]=[CH:10][C:11]([I:13])=[CH:12][N:7]3[C:5]=2[CH3:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 131735781N-(1-(1-Cyclopropyl-1-oxopropan-2-yl)-5-iodopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide

Product 1

HCID 896903982-Cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(1-(1-cyclopropyl-1-oxopropan-2-yl)-5-iodopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (30.5 g) in THF (300 mL) was added trifluoroacetic anhydride (18.3 mL) dropwise, and the mixture was stirred for 3 hr. The resulting precipitate was collected by filtration, and washed with diethyl ether to give a salt of the title compound as a white solid. The obtained solid was dissolved in 1 N sodium hydroxide, and the solution was extracted with ethyl acetate/THF. Then the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The obtained solid was washed with diisopropyl ether to give the title compound (17.7 g) as a yellow solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6db0c35485e640179f32a44cfd03d72d
Source dataset
uspto-grants-2016_09
Patent number
US09440987B2

Reaction notes

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