Iodine → tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

HRID 340423

反応式

HRID 340423 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Li]CCCC.[I:21]I.O>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[C:4]([I:21])[CH:3]=1

参加物

6

反応物 4

HCID 807IodineHCID 962WaterHCID 7330593(6-Chloro-pyridin-3-yl)-carbamic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate収率 32.3%

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

To the solution of tert-butyl (6-chloropyridin-3-yl)carbamate (160 g, 0.7 mol) in 1 L of anhydrous THF was added n-BuLi (600 mL, L5 ml) at −78° C. under N2 atmosphere. After the addition was finished, the solution was stirred at −78° C. for 30 min, and the solution of I2 (177.68 g, 0.7 mol) in 800 mL of anhydrous THF was added. Then the solution was stirred at −78° C. for 4 hrs, TLC indicated the reaction was over. Water was added for quench, and EtOAc was added to extract twice. The combined organic phases were washed with brine, dried over Na2SO4, filtered and purified by flash chromatography to afford 80 g of tert-butyl (6-chloro-4-iodopyridin-3-yl)carbamate as a yellow solid (32.3%).

後処理

  1. customat −78° C.
  2. additionAfter the addition
  3. stirringThen the solution was stirred at −78° C. for 4 hrs
  4. customfor quench
  5. additionEtOAc was added
  6. extractionto extract twice
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-051484aadb5545ff80213495b030f72d
出典データセット
uspto-grants-2014_11
特許番号
US08895586B2

関連ノート

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