(Prop-2-en-1-yl)stannane → 5-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

HRID 1857631노트

반응식

HRID 1857631 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8](I)[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1.[CH2:25]([Sn])[CH:26]=[CH2:27]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH2:27][CH:26]=[CH2:25])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1

참가 물질

4

반응물 2

HCID 15842380(Prop-2-en-1-yl)stannaneHCID 540909164-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester

생성물 1

HCID 542443075-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

반응 조건

온도
100 °C

실험 절차

To a suspension of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester (2.39 g in 12 mL N,N-dimethylformamide) and 0.183 g bis(triphenylphosphine)palladium(II) chloride was added 2.02 mL allyltin and the mixture heated to 100° C. on an oil bath. After 2 hours, the mixture was cooled, partitioned between ethyl acetate and water and the organic layer washed further with brine. Concentration of the dried (magnesium sulfate) organics and purification by flash chromatography on silica gel (hexane:ethyl acetate, 95:5; then 90:10) gave the title compound (1.4 g).

후처리

  1. temperaturethe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washthe organic layer washed further with brine
  4. dry with materialConcentration of the dried (magnesium sulfate) organics
  5. custompurification by flash chromatography on silica gel (hexane

출처 및 근거

ORD 기록
ord-58a59c8f2fcc46ff9b510fc4194b8886
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147088

반응 노트

불러오는 중…