Sodium Azide → 5-(Azidomethyl)isoquinoline

HRID 1861674ノート

反応式

HRID 1861674 の反応式
Cl[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.CCOC(C)=O>[N:13]([CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2)=[N+:14]=[N-:15]

参加物

5

反応物 2

HCID 33557Sodium Azide2 回HCID 120186945-(Chloromethyl)isoquinoline

生成物 1

HCID 120186955-(Azidomethyl)isoquinoline

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 0.0415 g (0.23 mmol) 16 in 3 mL DMF was added 0.0169 g (0.26 mmol) sodium azide. After a 3 h, an additional 0.0033g (0.05 mmol) portion of sodium azide was added. After 24 h at room temperature, the reaction mixture was diluted with 50 mL EtOAc and washed with 20 mL brine. The aqueous layer was extracted with 10 mL EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (10×175 mm silica gel, linear gradient 5-20% EtOAc:hexane) produced 17. 1H NMR (CDCl3, 400 MHz) δ 9.318 (s, 1H, ArH); 8.637 (d, 1H, J=6.10 Hz, ArH); 8.010 (d, 1H, J=7.94 Hz, ArH); 7.822 (d, 1H, J=6.10 Hz, ArH); 7.713 (d, 1H, J=7.02 Hz, ArH); 7.617 (dd, 1H, J=7.17, 8.09 Hz, ArH); 4.774 (s, 1H, ArH); MS (Electrospray): m/z 185.0 (M+H).

後処理

  1. waitAfter 24 h at room temperature
  2. washwashed with 20 mL brine
  3. extractionThe aqueous layer was extracted with 10 mL EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (10×175 mm silica gel, linear gradient 5-20% EtOAc:hexane)

出典と根拠

ORDレコード
ord-8532594578b346208285051fece14f70
出典データセット
uspto-grants-2003_03
特許番号
US06534510B2

反応ノート

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