Trifluoroacetic acid → 4-(6-fluoropyridin-3-yl)-1H-pyrrol-2(5H)-one

HRID 595921Notes

Reaction equation

HRID 595921 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:12][N:11](C(OC(C)(C)C)=O)[C:10](=[O:20])[CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:12][NH:11][C:10](=[O:20])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118046439tert-butyl 4-(6-fluoropyridin-3-yl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 1180452444-(6-fluoropyridin-3-yl)-1H-pyrrol-2(5H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(6-fluoropyridin-3-yl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (315 mg, 1.132 mmol) in DCM (4 mL) was added TFA (1 mL, 12.98 mmol). The reaction mixture was stirred at room temperature for 1 h. Reaction mixture was evaporated. Azeotrope with toluene (x=3) yielding 4-(6-fluoropyridin-3-yl)-1H-pyrrol-2(5H)-one. Proceed for next step. LCMS (m/z): 179.2 (MH+), 0.373 min. The crude yield was quantitative.

Workup

  1. customReaction mixture
  2. customwas evaporated

Sources & evidence

ORD record
ord-76423177b78842f4a17e4e42eecbd4dc
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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