1-[1-(4-fluorobenzyl)-4-nitro-1H-pyrrol-2-yl]ethanone → HCID 18363509, compound

HRID 381504Notes

Reaction equation

HRID 381504 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[C:8]2[C:15](=[O:17])[CH3:16])=[CH:4][CH:3]=1>[Pd]>[NH2:12][C:10]1[CH:9]=[C:8]([C:15](=[O:17])[CH3:16])[N:7]([CH2:6][C:5]2[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=2)[CH:11]=1

Participants

3

Reactant 1

HCID 183634661-[1-(4-fluorobenzyl)-4-nitro-1H-pyrrol-2-yl]ethanone

Product 1

HCID 18363509HCID 18363509, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a 1L round bottomed flask with a stirring bar and a balloon hydrogenation adapter was added 1-[1-(4-fluorobenzyl)-4-nitro-1H-pyrrol-2-yl]ethanone AVI-1-1 (8.00 g, 30.51 mmol) absolute EtOH (640 mL) and 10% Pd-C (2.24 g, 2.11 mmol). This mixture was hydrogenated at ambient temperature 24 h. The catalyst was removed by filtration and the EtOH was removed in vacuo. The semi-solid residue was chromatographed on silica gel using EtOAc as eluant to give 1-[4-amino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone AVI-2-1 as a yellow crystalline solid. 1H NMR (CDCl3) δ 2.34 (3H, s), 3.01 (2H, br s), 5.42 (2H, s), 6.46 (1H, d, j=2.0 Hz), 6.50 (1H, d, j=2.0 Hz), 6.98 (2H, m), 7.12 (2H, m).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe EtOH was removed in vacuo
  3. customThe semi-solid residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-fafe640ccc1f4985988f576243475fa6
Source dataset
uspto-grants-2001_10
Patent number
US06306891B1

Reaction notes

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