Calcium Chloride → 6'-Chloro-3-(trifluoromethyl)[2,3'-bipyridin]-5'-amine

HRID 968599Notes

Reaction equation

HRID 968599 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[N+:18]([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH2:18]

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 22030137HCID 22030137, compound

Product 1

HCID 220300306'-Chloro-3-(trifluoromethyl)[2,3'-bipyridin]-5'-amineYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6′-chloro-5′-nitro-3-trifluoromethyl-[2,3′]bipyridinyl (25 g, 0.082 mol) and calcium chloride (11 g, 0.1 mol) in ethanol (300 mL) and water (50 mL), add iron powder (45 g, 0.82 mol). Heat the solution to reflux for 1.5 hours, cool and filter through Celite. Concentrate the mixture under reduced pressure, re-dissolve in ethyl acetate (300 mL) and wash with brine (200 mL). Concentrate the solution under reduced pressure and purify by flash chromatography on silica gel (50/ether/50% hexane) to give the title compound (19 g, 85%) as a pale yellow solid.

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux for 1.5 hours
  3. temperaturecool
  4. filtrationfilter through Celite
  5. concentrationConcentrate the mixture under reduced pressure
  6. dissolutionre-dissolve in ethyl acetate (300 mL)
  7. washwash with brine (200 mL)
  8. concentrationConcentrate the solution under reduced pressure
  9. custompurify by flash chromatography on silica gel (50/ether/50% hexane)

Sources & evidence

ORD record
ord-099995b90fed4379a4b576934f41bf20
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

Loading…