Sodium hydride → HCID 4657444, compound

HRID 500647Notes

Reaction equation

HRID 500647 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br>CN(C=O)C>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 4657444HCID 4657444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromoindole (1.96 g, 10 mmol) was dissolved in 20 mL of DMF, 60%-NaH (0.44 g, 11 mmol) was added. It was stirred for 30 minutes, then 2-fluorobenzyl bromide (1.33 mL, 11 mmol) was added. Stirring continued at 50° C. for 5 hours. After dilution with EtOAc, the organic layer washed with brine (5×), dried over MgSO4. After evaporation to dryness, it was then dried under high vacuum to yield N-2-Fluorobenzyl-5-bromoindole in quantitative yield. The title compound was prepared by substituting N-2-Fluorobenzyl-5-bromoindole (3.04 g, 10 mmol) for 4-bromo-2-nitrophenylamine in EXAMPLE 2A. Crude material was purified by silica gel column chromatography, eluting with 2.5% EtOAc in hexane. 2.18 g of the title compound was obtained. MS: ESI(+) m/e 352.1 (M+H)+.

Workup

  1. stirringStirring
  2. waitcontinued at 50° C. for 5 hours
  3. washAfter dilution with EtOAc, the organic layer washed with brine (5×)
  4. dry with materialdried over MgSO4
  5. customAfter evaporation to dryness, it
  6. customwas then dried under high vacuum

Sources & evidence

ORD record
ord-82c62ed478bd4a338c07d6409dec7ffe
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

Loading…