Sodium hydride → HCID 22613232, compound

HRID 844369Notes

Reaction equation

HRID 844369 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:18][C:17]2[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 6764936-Bromoindole

Product 1

HCID 22613232HCID 22613232, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromoindole (J. Org. Chem. 1986, 51, 5106) (3.00 g, 15.3 mmol) in DMF (65 mL) was treated with NaH (734 mg of a 60% suspension in mineral oil, 18.4 mmol). After 30 min, 4-fluorobenzyl bromide (1.90 mL, 15.3 mmol) was added. When starting material was consumed, the reaction mixture was poured into 1N HCl and extracted with EtOAc (3×), the combined organic layers were dried (MgSO4) and concentrated. Chromatography of the residue (4:1/hexanes:EtOAc) provided the product.

Workup

  1. customwas consumed
  2. additionthe reaction mixture was poured into 1N HCl
  3. extractionextracted with EtOAc (3×)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customChromatography of the residue (4:1/hexanes:EtOAc) provided the product

Sources & evidence

ORD record
ord-56d2fc539c1549febbba8e4669b7d5bc
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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