Pyrrole → HCID 10821140, compound

HRID 2377065Notes

Reaction equation

HRID 2377065 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1.[OH-].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8027PyrroleHCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 10821140HCID 10821140, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of pyrrole (10.0 mL, 9.67 g, 144.13 mmol) in dichloromethane (200 mL) were added tetrabutylammonium bromide (46.5 g, 144.13 mmol), 4-fluorobenzyl bromide (17.7 mL, 158.54 mmol) and 50% NaOH aqueous solution (120 mL) with cooling in an ice-water bath. The resulting mixture was heated to reflux for 5 hr. After cooling down, it was quenched with saturated aqueous NH4Cl solution (200 mL), and extracted with dichloromethane (300 mL). The organic extract was dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Elution with dichloromethane:ethyl acetate:hexanes (1:1:5) provided the title compound (20 g, 79% yield). 1H NMR (CDCl3) δ ppm 6.96-7.09 (m, 4H), 6.67 (d, 2H, J=2.0 Hz), 6.19 (t, 2H, J=2.0 Hz), 5.03 (s, 2H). LCMS (APCI, M+H+): 176.1.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 5 hr
  4. temperatureAfter cooling down
  5. customit was quenched with saturated aqueous NH4Cl solution (200 mL)
  6. extractionextracted with dichloromethane (300 mL)
  7. extractionThe organic extract
  8. dry with materialwas dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by flash chromatography
  11. washElution with dichloromethane:ethyl acetate:hexanes (1:1:5)

Sources & evidence

ORD record
ord-dd3efae3d7e448aabe4a57dbed660c52
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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