1-Bromo-3-chloropropane → HCID 59612976, compound

HRID 445756Notes

Reaction equation

HRID 445756 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][CH2:14]2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride2×HCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Product 1

HCID 59612976HCID 59612976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-bromo-pyridin-3-yl)-acetonitrile (Stage 220.1.3, 1.37 mmol) in dry DMF (10 ml) was added 55% sodium hydride in oil (1.507 mmol). After 30 min stirring at rt was added 1-bromo-3-chloropropane (1.507 mmol). The RM was stirred for 1 h at rt then was added 55% sodium hydride in oil (1.507 mmol). The RM was stirred for 1 h at it then quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine (2×), dried over Na2SO4, filtered and evaporated. The residue was taken in DMA and purified by preparative HPLC. The fractions containing product were basified with NaHCO3, concentrated and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a red oil. (HPLC: tR 2.86 min (Method A); M+H=237, 239 MS-ES)

Workup

  1. stirringThe RM was stirred for 1 h at rt
  2. stirringThe RM was stirred for 1 h at it
  3. customthen quenched with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine (2×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. custompurified by preparative HPLC
  10. additionThe fractions containing product
  11. concentrationconcentrated
  12. extractionextracted with EtOAc (2×)
  13. washThe combined organic layers were washed with brine
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. customevaporated
  17. customdried under vacuum

Sources & evidence

ORD record
ord-2b239df02470480188e03f8c4fd29cb1
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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