HCID 59648478, compound → HCID 59648666, compound

HRID 1363299Notes

Reaction equation

HRID 1363299 reaction equation
[CH:1]([C:3]1[C:7]2[NH:8][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][C:6]=2[O:5][CH:4]=1)=[CH2:2]>CCOC(C)=O.[Pd]>[CH2:1]([C:3]1[C:7]2[NH:8][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][C:6]=2[O:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 59648478HCID 59648478, compound

Product 1

HCID 59648666HCID 59648666, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 3-vinyl-4H-furo[3,2-b]pyrrole-5-carboxylate (105 mg, 0.51 mmol) in EtOAc (8 mL) in a 40-mL scintillation vial was treated with 10% Pd/C (˜15 mg) and a balloon of H2. The system was evacuated and refilled three times with H2 before hydrogenating at rt for 6 h. The catalyst was removed by filtration over Celite® and the filtrate was concentrated. The crude product was purified by flash chromatography (0-10% EtOAc/heptane) to give ethyl 3-ethyl-4H-furo[3,2-b]pyrrole-5-carboxylate (96 mg, 91%). 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (t, J=7.54 Hz, 3H), 1.36-1.42 (m, 3H), 2.57-2.64 (m, 2H), 4.33-4.40 (m, 2H), 6.76 (d, J=1.66 Hz, 1H), 7.31 (t, J=1.12 Hz, 1H); LCMS-MS (ESI+) 207.83 (M+H).

Workup

  1. customThe system was evacuated
  2. additionrefilled three times with H2 before hydrogenating at rt for 6 h
  3. customThe catalyst was removed by filtration over Celite®
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by flash chromatography (0-10% EtOAc/heptane)

Sources & evidence

ORD record
ord-e209ad2227554174a5214fab888252cc
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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