Triphenylphosphine → 3-Cyano-2-fluoropyridine

HRID 1178931Notes

Reaction equation

HRID 1178931 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-9daca0f9c8a94c3692cb5df952bc2f71
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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