Sodium hydride → 3-[1-(2-Bromomethyl-benzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-furan-2,5-dione

HRID 1859198Notes

Reaction equation

HRID 1859198 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:26])[O:12][C:13](=[O:25])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)=[CH:2]1.[H-].[Na+].Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][Br:38]>CN(C)C=O>[Br:38][CH2:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:26])[O:12][C:13](=[O:25])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66665o-Bis(bromomethyl)benzeneHCID 148557143-(1-Methyl-indol-3-yl)-4-(indol-3-yl)-furan-2,5-dione

Product 1

HCID 221232673-[1-(2-Bromomethyl-benzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-furan-2,5-dioneYield 17.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 3-(indol-3-yl)-4-(1-methyl-indol-3-yl)-furan-2,5-dione (1.0 g, 3 mmol) and sodium hydride (154 mg, 3.5 mmol, 55-60% dispersion in oil) in dimethylformamide (20 mL) was stirred and cooled to 0° C., under a stream of nitrogen. After 35 min the solution was transferred to a dropping funnel and added slowly, over 40 min, to a solution of 1,2-bis-bromomethyl-benzene (3.8 g, 14.5 mmol) in dimethylformamide (6 mL). The resulting solution was stirred for 1 h at room temperature under a stream of nitrogen. The reaction was quenched by adding NaHCO3 (aq), and extracted with ethyl acetate. The organic phase was washed with several portions of water and dried (MgSO4). Evaporation followed by chromatography on silica (ethyl acetate:heptane, 3:7) afforded 270 mg of the desired product.

Workup

  1. stirringThe resulting solution was stirred for 1 h at room temperature under a stream of nitrogen
  2. customThe reaction was quenched
  3. additionby adding NaHCO3 (aq)
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with several portions of water
  6. dry with materialdried (MgSO4)
  7. customEvaporation

Sources & evidence

ORD record
ord-8157b277b9ec44f4b6e9471f085a20cd
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Reaction notes

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