Triphenylphosphine → 3-Cyano-2-fluoropyridine

HRID 736993ノート

反応式

HRID 736993 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-f785c08da873469b9a460065bb3c21ab
出典データセット
uspto-grants-2009_09
特許番号
US07595339B2

反応ノート

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