Sodium hydride → HCID 90410366, compound

HRID 871096Notes

Reaction equation

HRID 871096 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 242292566-Bromo-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 90410366HCID 90410366, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-1H-pyrrolo[3,2-b]pyridine (400 mg, 2.030 mmol) and sodium hydride (60% in mineral oil) (89 mg, 2.233 mmol) in 4 mL N,N-dimethylformamide was stirred at ambient temperature for 10 minutes and 1-(bromomethyl)-3-fluorobenzene (384 mg, 2.030 mmol) was added. The mixture was heated at 100° C. for 3 hours. The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on Analogix IntelliFlash280 eluting with 10 to 70% ethyl acetate/hexanes to give the title compound.

Workup

  1. temperatureThe mixture was heated at 100° C. for 3 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on Analogix IntelliFlash280
  8. washeluting with 10 to 70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-18f5165278144650a28e54bfa6e37a18
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

Loading…