Trifluoroacetic anhydride → HCID 89995741, compound

HRID 523100Notes

Reaction equation

HRID 523100 reaction equation
[Br:1][C:2]1[N:6]([CH3:7])[C:5](/[CH:8]=[N:9]/O)=[N:4][CH:3]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]#[N:9])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 136490486HCID 136490486, compound

Product 1

HCID 89995741HCID 89995741, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(E)-5-Bromo-1-methyl-1H-imidazole-2-carbaldehyde oxime (Preparation 155, 38 mg, 0.186 mmol) and TEA (39 uL, 0.279 mmol) was stirred in THF (6 mL) and cooled at 0° C., TFAA (28 uL, 0.205 mmol) was added. Then the mixture was stirred at 60° C. under microwave irradiation for 3 hours. The reaction was purified directly by Biotage silica gel column chromatography eluting with 20% EtOAc in cyclohexanes to give the title compound as yellow solid (15 mg, 43%).

Workup

  1. customThe reaction was purified directly by Biotage silica gel column chromatography
  2. washeluting with 20% EtOAc in cyclohexanes

Sources & evidence

ORD record
ord-24d1050e58b24e10befabc1404e94d26
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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