Triphenylphosphine → 3-Cyano-2-fluoropyridine

HRID 1178931

반응식

HRID 1178931 반응식
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]

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 2523672-Fluoronicotinamide

생성물 1

HCID 27832543-Cyano-2-fluoropyridine수율 64.8%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 63651,1-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9daca0f9c8a94c3692cb5df952bc2f71
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276516B2

연결된 노트

불러오는 중…