Dichloromethane → 5-Bromo-6-methoxy-3-pyridineacetonitrile

HRID 2204335Notes

Reaction equation

HRID 2204335 reaction equation
[Br:1][C:2]1[C:3]([O:10][CH3:11])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[C-:12]#[N:13].[Na+].C(Cl)Cl.C([O-])(O)=O.[Na+]>O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:12]#[N:13])[CH:5]=[N:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 585395103-Bromo-5-bromomethyl-2-methoxy-pyridine

Product 1

HCID 585393925-Bromo-6-methoxy-3-pyridineacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-bromo-5-bromomethyl-2-methoxy-pyridine (Step AM2) (3.9 g, 14.0 mmol) in H2O was added NaCN (750 mg, 15.3 mmol) and the mixture was stirred at 50° C. for 1.5 h. CH2Cl2 and a saturated aqueous solution of NaHCO3 were added and the phases were separated. The organic layer was washed with H2O and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (heptane/EtOAc, 80:20→0:100). tR: 0.88 min (LC-MS 1).

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (heptane/EtOAc, 80:20→0:100)

Sources & evidence

ORD record
ord-5aa2b8b6860644b6bd34ff05eabadaa9
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…