Azidotrimethylsilane → 3-Chloro-6-(2H-1,2,3-triazol-4-yl)isoquinoline

HRID 523062ノート

反応式

HRID 523062 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[CH:13])=[CH:7][CH:6]=2.[N:14]([Si](C)(C)C)=[N+:15]=[N-:16]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:13]=[N:16][NH:15][N:14]=1)=[CH:7][CH:6]=2

参加物

5

反応物 2

HCID 78378AzidotrimethylsilaneHCID 899955703-Chloro-6-ethynylisoquinoline

生成物 1

HCID 899956273-Chloro-6-(2H-1,2,3-triazol-4-yl)isoquinoline収率 61%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

3-chloro-6-ethynylisoquinoline (Preparation 50, 120 mg, 0.64 mmol) was dissolved in dry DMF (1 mL). Azidotrimethylsilane (1 mL, 7.5 mmol) was added and the reaction stirred at 120° C. for 2 hours. The reaction was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic solution was washed with water (20 mL), brine (20 mL), dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 2% 7N NH3 in methanol in DCM followed by elution through an SCX-2 column using 50% methanol in chloroform followed by 50% 7N NH3 in methanol in chloroform to afford the title compound as a pale brown powder (90 mg, 61%).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. washThe organic solution was washed with water (20 mL), brine (20 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 2% 7N NH3 in methanol in DCM
  7. washfollowed by elution through an SCX-2 column

出典と根拠

ORDレコード
ord-c19af088cac24e75b2d62f82f2dc7351
出典データセット
uspto-grants-2016_05
特許番号
US09334286B2

反応ノート

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