Azidotrimethylsilane → HCID 178487641、化合物

HRID 915905ノート

反応式

HRID 915905 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]\[N+:11]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[Si]([N:24]=[N+:25]=[N-])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:24]=[N:25][NH:11][CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

参加物

5

反応物 3

HCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 68881182HCID 68881182、化合物

生成物 1

HCID 178487641HCID 178487641、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A solution of 2-{2-methoxy4-[(Z)-2-nitroethenyl]phenyl}pyridine (0.23 g, 0.89 mmol) and TMSN3 (0.18 mL, 1.34 mmol) in DMF (1 mL) was heated to slowly to 50° C. while TBAF (0.98 mL, 1.0 M in THF, 0.98 mol) was added dropwise over 20 min. The resulting reaction mixture was continued to stir at 50° C. for 30 min. The mixture was partitioned between sat. NaHCO3 (20 mL) and EtOAc (60 mL). The phases were separated and the aqueous layer was extracted with EtOAc (3×60 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified on silica gel (20:1 hexane-ethyl acetate) to afford a yellow solid.

後処理

  1. additionwas added dropwise over 20 min
  2. customThe resulting reaction mixture
  3. customThe mixture was partitioned between sat. NaHCO3 (20 mL) and EtOAc (60 mL)
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×60 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (20:1 hexane-ethyl acetate)
  10. customto afford a yellow solid

出典と根拠

ORDレコード
ord-d71f459474f448798b53a85f4873100b
出典データセット
uspto-grants-2007_09
特許番号
US07268151B2

反応ノート

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