Trifluoroacetic anhydride → p-Toluenesulfonic acid

HRID 2202833Notes

Reaction equation

HRID 2202833 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:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH3:6])[CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:29]>C1COCC1>[C:21]1([CH3:24])[CH:20]=[CH:19][C:18]([S:15]([OH:16])(=[O:17])=[O:29])=[CH:23][CH:22]=1.[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

5

Reactant 2

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

Product 2

HCID 6101p-Toluenesulfonic acidHCID 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-methylbenzene sulfonamide (30.5 g) in THF (300 ml) was added trifluoroacetic anhydride (18.3 ml) dropwise. After 3 h, the resulting precipitate was collected by filtration, and washed with ether to give p-toluenesulfonic acid salt of the title compound as a white solid. The solid obtained was dissolved in a mixture of 1 M NaOH, EtOAc and THF. Then the organic layer was washed with brine, dried over MgSO4 and concentrated. The resulting solid was triturated with IPE, and collected to give the title compound (17.7 g) as a pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-938062ca7cf144798bd98ab7d67b0abb
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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