Potassium Iodide → HCID 89656291、化合物

HRID 2206862ノート

反応式

HRID 2206862 の反応式
[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)\[C:4]#[N:5].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19]Br)[N:14]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CN(C=O)C>[Br:12][C:13]1[N:14]=[C:15]([CH2:19][O:1]/[N:2]=[C:3](/[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)\[C:4]#[N:5])[CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 5464219N-Hydroxybenzimidoyl cyanideHCID 129547962-Bromo-6-(bromomethyl)pyridine

生成物 1

HCID 89656291HCID 89656291、化合物収率 87%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (6.0 g, 41.1 mmol, 1 eq.) in 80 ml of acetonitrile and 10 ml of DMF, was added 2-bromo-6-(bromomethyl)pyridine (10.3 g, 41.1 mmol, 1.0 eq.) followed by potassium iodide (681 mg, 4.11 mmol, 0.1 eq.) and caesium carbonate (20.1 g, 61.1 mmol, 1.5 eq.). The reaction was stirred 4 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. After separation, the organic phase was dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(6-bromopyridin-2-yl)methoxy]imino}(phenyl)acetonitrile (11.3 g, 86% yield) as a white solid.

後処理

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washsubsequently washed with H2O and brine
  4. customAfter separation
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-8e746cabfcd04a9c8d420d34a94233d6
出典データセット
uspto-grants-2016_06
特許番号
US09375010B2

反応ノート

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