Pyridine → 6-Chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinonitrile

HRID 1020823Notes

Reaction equation

HRID 1020823 reaction equation
[Cl:1][C:2]1[C:10]([CH:11]2[CH2:13][CH2:12]2)=[CH:9][C:5]([C:6]([NH2:8])=O)=[C:4]([O:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[N:3]=1.O=P(Cl)(Cl)Cl.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(#N)C>[Cl:1][C:2]1[C:10]([CH:11]2[CH2:12][CH2:13]2)=[CH:9][C:5]([C:6]#[N:8])=[C:4]([O:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 866617306-Chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinamide

Product 1

HCID 866617316-Chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinamide (180 mg, 0.6 mmol) in acetonitrile (20 mL) was added POCl3 (276 mg, 1.8 mmol) and pyridine (285 mg, 3.6 mmol). After stirred at r.t for 2 hrs, the mixture was poured into aq. NaHCO3, extracted with EtOAc. The separated organics was dried and concentrated in vacuo to afford crude 6-chloro-5-cyclopropyl-2-(2-isopropoxyethoxy)nicotinonitrile (150 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe separated organics was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed49707342c0463fb59e474da486fb85
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

Loading…