Sodium Cyanide → Methyl 5-cyano-2-(4-fluorophenoxy)nicotinate

HRID 1293201ノート

反応式

HRID 1293201 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C-:20]#[N:21].[Na+]>C(#N)CC.[Cu](I)I>[C:20]([C:2]1[CH:3]=[N:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:21]

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 57572305HCID 57572305、化合物

生成物 1

HCID 69051385Methyl 5-cyano-2-(4-fluorophenoxy)nicotinate収率 71.3%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 7854Propionitrile溶媒

実験手順

A mixture of methyl 5-bromo-2-(4-fluorophenoxy)nicotinate (step 1, 163 mg, 0.50 mmol), sodium cyanide (49 mg, 1.0 mmol), tetrakis(triphenylphohphine) palladium(0) (29 mg, 0.025 mmol), and copper iodide (9.5 mg, 0.05 mmol) in propionitrile (4.0 mL) was heated under reflux for 4.5 h with stirring. The reaction mixture was filtered through a pad of Celite®. The filtrate was partitioned between water (10 mL) and dichloromethane (30 mL). The organic phase was separated, dried (sodium sulfate), and concentrated. The residue was purified by TLC plate developing with hexane/ethyl acetate (3/1) to afford 97 mg (71%) of the title compound: 1H-NMR (CDCl3) δ 8.5 (2H, m), 7.14 (2H, d, J=1.2 Hz), 7.12 (2H, s), 3.99 (3H, s); MS (ESI) m/z 272 (M+).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 h
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. customThe filtrate was partitioned between water (10 mL) and dichloromethane (30 mL)
  5. customThe organic phase was separated
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by TLC plate

出典と根拠

ORDレコード
ord-78234e9beb5d4c90a635478c61814a85
出典データセット
uspto-grants-2007_07
特許番号
US07238714B2

反応ノート

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