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

HRID 340423

반응식

HRID 340423 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-051484aadb5545ff80213495b030f72d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895586B2

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