Sodium Iodide → HCID 69746023, compound

HRID 397968Notes

Reaction equation

HRID 397968 reaction equation
BrC[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Na+].[I-].[C:12]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[H-].[Na+].[Br-].[Na+].[I-].[Cl-].[NH4+]>COCCOC>[CH2:21]([O:20][C:12](=[O:19])[CH:13]([C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:22]

Participants

8

Reactant 6

HCID 5238Sodium IodideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 6403092-bromo-1-(1H-pyrrol-2-yl)ethanoneHCID 19734138HCID 19734138, compound

Product 1

HCID 69746023HCID 69746023, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

2-Bromo-1-(1H-pyrrol-2-yl)-ethanone (1.00 mmol, 0.19 g) in DME (3 ml) was treated with NaI (1.00 mmol, 0.15 g), and stirred vigorously for 30 minutes. A solution of diethyl malonate (1.50 mmol, 0.2 ml), NaH (1.00 mmol, 40 mg of 60% in oil), and DME (3 ml) was added to the bromide-NaI mixture, and held at room temperature overnight. Saturated aqueous ammonium chloride (10 ml) was added, then the mixture was extracted with ethyl acetate (2×25 ml). The combined organic extracts washed with brine (25 ml), then concentrated under reduced pressure. Purification of the residue by silica gel chromatography provided 0.21 g (79%) of 2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ9.76 (1H, s), 7.04 (1H, dt, J=2.7, 1.3), 7.00 (1H, ddd, J=3.8, 2.4, 1.3), 6.30-6.26 (1H, m), 4.21 (4H, m), 4.02 (1H, t, J=7.3), 3.45 (2H, d, J=7.3), 1.25 (6H, t, J=7.1).

Workup

  1. waitheld at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate (2×25 ml)
  3. washThe combined organic extracts washed with brine (25 ml)
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-ceb8aed32aa842d8a4a45c270fa8d530
Source dataset
uspto-grants-2003_08
Patent number
US06610730B2

Reaction notes

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