Iodine → [1-(6-Chloro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 1640906ノート

反応式

HRID 1640906 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[I:23]I>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[C:4]([I:23])[CH:3]=1

参加物

5

反応物 3

HCID 807IodineHCID 86640491HCID 86640491、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 86640498[1-(6-Chloro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Dissolve tert-butyl 1-(6-chloropyridin-3-yl)ethylcarbamate (3.77 g, 14.7 mmol) in THF (60 mL). Add tert-butyllithium (1.7 M heptane solution, 25.9 mL, 44.0 mmol) at −78° C. under N2. Stir the reaction solution for 0.5 h at −78° C. Add a solution of iodine (5.59 g, 22.0 mmol) in THF (44 mL) dropwise over 30 min under N2 at −78° C. Stir the resulting solution at −78° C. for 1 h, then from −78° C. to RT for 1 h. Quench the reaction with water. Extract with ethyl acetate. Wash the organic layer with water and saturated aqueous sodium chloride. Dry over MgSO4. After filtration, concentrate and purify the crude by FCC (0.1% to 1% 2 M NH3 methanol solution/CH2Cl2) to afford the title compound (1.34 g, 24%) with 98% HPLC purity. MS (ES) m/z 383 [M+1]+

後処理

  1. customat −78° C.
  2. stirringStir the resulting solution at −78° C. for 1 h
  3. waitfrom −78° C. to RT for 1 h
  4. customQuench
  5. customthe reaction with water
  6. extractionExtract with ethyl acetate
  7. washWash the organic layer with water and saturated aqueous sodium chloride
  8. dry with materialDry over MgSO4
  9. filtrationAfter filtration
  10. concentrationconcentrate
  11. custompurify the crude by FCC (0.1% to 1% 2 M NH3 methanol solution/CH2Cl2)

出典と根拠

ORDレコード
ord-9d381872a5ae4e6e935ab5c84f080274
出典データセット
uspto-grants-2012_02
特許番号
US08114872B2

反応ノート

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