Triphenylphosphine → 3-Cyano-2-fluoropyridine

HRID 736993

반응식

HRID 736993 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-f785c08da873469b9a460065bb3c21ab
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595339B2

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