Propargyl alcohol → HCID 89924003, 화합물

HRID 1500938노트

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HRID 1500938 반응식
[Cl:1][C:2]1[CH:14]=[C:13](I)[C:5]([NH:6][CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([F:16])[CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19]>CCN(CC)CC.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.[Cu]I>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5](=[C:4]([F:16])[CH:3]=1)[N:6]([CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:18]([CH2:17][OH:20])=[CH:19]2

참가 물질

6

반응물 2

HCID 7859Propargyl alcoholHCID 899240084-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline

생성물 1

HCID 89924003HCID 89924003, 화합물수율 95.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A mixture of 4-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline (450 mg, 1.2 mmol) and prop-2-yn-1-ol (135 mg, 2.4 mmol) in Et3N (20 ml) was degassed and refluxed under N2 atmosphere. PdCl2(PPh3)2 (90 mg, 0.12 mmol) and CuI (45 mg, 0.24 mmol) were added successively to the reaction mixture. After being stirred under reflux overnight, the mixture was concentrated in vacuo and the residue was poured into water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4 and then concentrated in vacuo. The residue was purified by preparative-TLC (PE: EtOAc=5:1) to give {5-chloro-7-fluoro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methanol as a yellow solid (350 mg, yield: 95%).

후처리

  1. customwas degassed
  2. temperaturerefluxed under N2 atmosphere
  3. temperatureunder reflux overnight
  4. concentrationthe mixture was concentrated in vacuo
  5. additionthe residue was poured into water
  6. extractionextracted with EtOAc (50 mL×3)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative-TLC (PE: EtOAc=5:1)

출처 및 근거

ORD 기록
ord-1b7f992032a34b73941a164c3a4a477a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206191B2

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