Benzyl Bromide → Methyl 1-benzyl-4-formyl-5-iodo-1H-pyrrole-2-carboxylate

HRID 1952537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952537
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[NH:6][C:7]=1[I:8])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([N:6]1[C:7]([I:8])=[C:3]([CH:1]=[O:2])[CH:4]=[C:5]1[C:9]([O:11][CH3:12])=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86664848Methyl 4-formyl-5-iodo-1H-pyrrole-2-carboxylate

Produkt 1

HCID 86664847Methyl 1-benzyl-4-formyl-5-iodo-1H-pyrrole-2-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4 (0.72 g, 2.6 mmol) in acetone (20 mL) was added K2CO3 (0.71 g, 5.1 mmol). The resulting mixture was stirred for 30 minutes at room temperature. Benzyl bromide (0.46 mL, 3.8 mmol) was added dropwise to the reaction mixture and was then refluxed for 16 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between ethyl acetate and water. The combined organic layer was dried over anhydrous MgSO4, filtered and then concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 5 as a white solid (0.85 g, 90%). 1H NMR (CDCl3) δ 9.66 (s, 1H), 7.50 (s, 1H), 7.24-7.25 (m, 3H), 6.98 (d, J=7.6 Hz, 2H), 5.75 (s, 2H), and 3.72 (s, 3H); 13C NMR (CDCl3) δ 186.98, 160.33, 136.43, 128.97, 128.22, 127.84, 127.10, 126.59, 119.32, 92.81, 52.81, and 52.11.

Aufarbeitung

  1. temperaturewas then refluxed for 16 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customMPLC purification (Hexanes:EtOAc/80:20) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-f3484ed8c7034684a5dbf6c023f6adae
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404728B2

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