5-Bromoisatin → HCID 28492568, compound

HRID 1407516Notes

Reaction equation

HRID 1407516 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].Br.Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:6](=[O:11])[C:5]2=[O:12]

Participants

5

Reactant 3

HCID 68895-BromoisatinHCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromide

Product 1

HCID 28492568HCID 28492568, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromoisatin (10.0 g, 44.4 mmol) in anhydrous N,N-dimethylformamide (100 mL) at 0° C. was added slowly sodium hydride (60% w/w dispersion in mineral oil, 3.90 g, 97.7 mmol). The solution was stirred for 30 min and 2-(bromomethyl)pyridine hydrobromide (11.2 g, 44.4 mmol) was added. The solution was stirred at ambient temperature for 16 h and poured into ice water (1.3 L) with vigourous stirring, causing a precipitate to be deposited. The solid was collected by filtration to afford 5-bromo-1-(pyridin-2-ylmethyl)-1H-indole-2,3-dione (4.93 g, 35%) as a orange solid: 1H NMR (300 MHz, CDCl3) δ 8.55-8.50 (m, 1H), 7.72-7.56 (m, 1H), 7.34-7.28 (m, 1H), 7.25-7.18 (m, 1H), 6.93-6.88 (m, 1H), 5.03-4.99 (m, 2H).

Workup

  1. stirringThe solution was stirred at ambient temperature for 16 h
  2. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-4d8ef93eb8e646d3a6b99f1a9ce89198
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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