Trifluoroacetic anhydride → 4-((4-Methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carbonitrile

HRID 1896876Notes

Reaction equation

HRID 1896876 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]=[C:11]([C:23]([NH2:25])=O)[CH:10]=2)=[CH:5][CH:4]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]=[C:11]([C:23]#[N:25])[CH:10]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 585628514-((4-Methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxamide

Product 1

HCID 585625264-((4-Methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carbonitrile

Procedure

A solution of 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxamide (9 g, 24 mmol) from above step B, and TEA (10 mL, 72 mmol) was treated with trifluoroacetic anhydride (4.35 mL, 31.3 mmol) at room temperature and stirred for 2 h (completion of reaction monitored by LCMS). Solvent was removed under vacuum and the residue was purified by recrystallization from EtOAc/Hex to give the title compound.

Workup

  1. custom(completion of reaction monitored by LCMS)
  2. customSolvent was removed under vacuum
  3. customthe residue was purified by recrystallization from EtOAc/Hex

Sources & evidence

ORD record
ord-679d0b26dff14cc5a1f3a17c9c365ef2
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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