Triphenylphosphine → 3-Cyano-2-fluoropyridine

HRID 1178931

反応式

HRID 1178931 の反応式
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]

参加物

5

反応物 2

HCID 11776TriphenylphosphineHCID 2523672-Fluoronicotinamide

生成物 1

HCID 27832543-Cyano-2-fluoropyridine収率 64.8%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9daca0f9c8a94c3692cb5df952bc2f71
出典データセット
uspto-grants-2007_10
特許番号
US07276516B2

関連ノート

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