Ethyl Acetate → HCID 58380548, compound

HRID 1259360Notes

Reaction equation

HRID 1259360 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH2:16]([N:23]1[C:27]2=[C:28]([N+:35]([O-:37])=[O:36])[C:29](O)=[C:30]([CH3:33])[C:31](=[O:32])[N:26]2[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>C(Cl)Cl>[CH2:16]([N:23]1[C:27]2=[C:28]([N+:35]([O-:37])=[O:36])[C:29]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:30]([CH3:33])[C:31](=[O:32])[N:26]2[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 583805271-Benzyl-7-hydroxy-6-methyl-8-nitro-2,3-dihydroimidazo[1,2-A]pyridin-5(1H)-one

Product 1

HCID 58380548HCID 58380548, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triflic anhydride (2.8 g, 0.010 mol) was added to a stirred solution of 1-benzyl-7-hydroxy-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (2 g, 0.007 mol) and TEA (1.34 g, 0.013 mol) in DCM (40 mL) at −78° C. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was monitored by TLC (100% ethyl acetate). The reaction mixture was partitioned between DCM and water. The organic layer was washed with NaHCO3 solution, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 2.5 g of the product (89% yield).

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic layer was washed with NaHCO3 solution, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-564b58265f23499d85252fbc82ac23b6
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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