Trifluoroacetic acid → HCID 90409033, compound

HRID 516588Notes

Reaction equation

HRID 516588 reaction equation
C(OC([NH:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=2)[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[CH:28]=[CH2:29])=O)(C)(C)C.FC(F)(F)C(O)=O>ClC(Cl)C>[NH2:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=2)[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[CH:28]=[CH2:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90408958HCID 90408958, compound

Product 1

HCID 90409033HCID 90409033, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Methyl 4-(tert-butoxycarbonylamino)-6-(4-chloro-3-fluorophenyl)-5-fluoro-3-vinylpicolinate (0.966 g, 2.274 mmol) was dissolved in dichloroethane (11 mL) and trifluoroacetic acid (3.50 mL, 45.5 mmol) was added. After 4 h at room temperature, the reaction mixture was concentrated under vacuum then coevaporated with additional dichloroethane twice more. The residue was purified by flash chromatography (SiO2, eluting with 7-60% ethyl acetate in hexanes) to provide the title compound as a white solid (0.705 g, 95%).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customThe residue was purified by flash chromatography (SiO2, eluting with 7-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-36dd011824fc4f39875f24c0aaf64ee0
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

Loading…