Triphenylphosphine → 3-Cyano-2-fluoropyridine

HRID 736993Notes

Reaction equation

HRID 736993 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[N:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=O>ClC(Cl)C.C(Cl)(Cl)(Cl)Cl>[F:20][C:21]1[N:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]#[N:25]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 2523672-Fluoronicotinamide

Product 1

HCID 27832543-Cyano-2-fluoropyridineYield 64.8%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Add resin bound triphenylphosphine (4.0 g, 12.0 mmol) to a solution of 2-fluoro-nicotinamide (0.6 g, 4.3 mmol) in dichloroethane (20.0 mL) and carbon tetrachloride (20.0 mL). Reflux for 18 hours, cool to RT, filter, and concentrate the filtrate under vacuum. Purify by flash column on silica gel eluting with 10-60% EtOAc in hexanes to give the title compound (0.34 g, 64%). MS (ES) 123.1 (M+1)+. 1H NMR (400 MHz, CHCl3) δ 8.46 (m, 1H), 8.09 (m, 1H), 7.37 (m, 1H).

Workup

  1. temperatureReflux for 18 hours
  2. filtrationfilter
  3. concentrationconcentrate the filtrate under vacuum
  4. customPurify by flash column on silica gel eluting with 10-60% EtOAc in hexanes

Sources & evidence

ORD record
ord-f785c08da873469b9a460065bb3c21ab
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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