Methyl 5-bromofuran-2-carboxylate → HCID 67394175, compound

HRID 1023731Notes

Reaction equation

HRID 1023731 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH2:14])=[O:13])[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].Br[C:16]1[O:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=1>>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:14][C:16]2[O:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:17]=2)=[O:13])[O:7][C:8]=1[CH:9]([CH3:10])[CH3:11])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 599633Methyl 5-bromofuran-2-carboxylateHCID 58420521HCID 58420521, compound

Product 1

HCID 67394175HCID 67394175, compoundYield 49%

Procedure

4,5-Diisopropylfuran-2-carboxamide (55 mg, 0.282 mmol) and methyl 5-bromofuran-2-carboxylate (116 mg, 0.566 mmol) were coupled. The reaction mixture was treated in a conventional manner, and the resultant was purified by silica gel chromatography [hexane-ethyl acetate (9:1)] and recrystallized to obtain methyl 5-[(4,5-diisopropylfuran-2-carbonyl)amino]-2-furancarboxylate (44 mg, 49%) and the collected starting material (26 mg, 47%) as colorless needles.

Workup

  1. additionThe reaction mixture was treated in a conventional manner
  2. customthe resultant was purified by silica gel chromatography [hexane-ethyl acetate (9:1)]
  3. customrecrystallized

Sources & evidence

ORD record
ord-3851346ab129425385114b7da412f2e9
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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