Trifluoroacetic acid → HCID 178470493, compound

HRID 873803Notes

Reaction equation

HRID 873803 reaction equation
C1C(=O)N([I:8])C(=O)C1.C(O)(C(F)(F)F)=O.[NH:16]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=[N:17]1>CC#N>[I:8][C:19]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:16][NH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 7147518Ethyl 1H-pyrazole-3-carboxylate

Product 1

HCID 178470493HCID 178470493, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NIS (8.83 g, 39.2 mmol) and TFA (0.825 mL, 10.70 mmol) were added to a stirred solution of ethyl 1H-pyrazole-5-carboxylate (5 g, 35.7 mmol) in CH3CN (120 mL) under Ar. The reaction mixture was stirred for 6 hr at rt, concentrated, diluted with a saturated aqueous solution of NaHCO3, and extracted with EtOAc. The combined organic layers were washed with a saturated aq. NaHCO3 solution, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 10-50%) to afford the title product (8.31 g, 31.2 mmol, 88% yield) as a white solid. tR: 3.47 min (HPLC 1); tR: 0.72 min (LC-MS 2); ESI-MS: 267 [M+H]+ (LC-MS 2); Rf=0.55 (hexane/EtOAc 1:1).

Workup

  1. concentrationconcentrated
  2. additiondiluted with a saturated aqueous solution of NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with a saturated aq. NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 10-50%)

Sources & evidence

ORD record
ord-f20a1818806442908d1a049c6416c60f
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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