Lead diacetate → 5-(2-Diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one

HRID 2365125Notes

Reaction equation

HRID 2365125 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=4)[NH:19][C:18]3=[O:27])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:28])[CH3:2].C([O-])(=O)C.[Pb+2].C([O-])(=O)C.[OH-].[Na+]>C(O)(=O)C>[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9]2[NH:12][C:13]([CH:16]=[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=4)[NH:19][C:18]3=[O:27])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:28])[CH3:30]

Participants

5

Reactant 3

HCID 9317Lead diacetateHCID 14798Sodium HydroxideHCID 666067185-(2-(Diethylamino)ethyl)-2-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 666073095-(2-Diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-oneYield 21.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (150 mg, 0.366 mmol) in acetic acid (3.5 ml) was cooled to 15° C. in an ice-water bath. The mixture was added with lead acetate (130 mg, 0.293 mmol) and stirred for 2.5 hours at room temperature. The mixture was added with 1N aqueous sodium hydroxide solution (60 ml) and extracted with a 5 to 1 solvent mixture of dichloromethane and methanol (40 ml×4). The extracts were combined, washed by brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to give 5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (32 mg) as a yellow solid.

Workup

  1. extractionextracted with a 5 to 1 solvent mixture of dichloromethane and methanol (40 ml×4)
  2. washwashed by brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9149a3ea42a4890b892331cc4a00ba1
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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