1-Iodo-4-(2-methyl-1-methylene-propyl)-benzene → (1R,2R)-5'-fluoro-2-(4-iodophenyl)-2-isopropylspiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805309노트

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HRID 1805309 반응식
[N+](=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[NH:5][C:4]1=[O:13])=[N-].[I:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH:23]([CH3:25])[CH3:24])=[CH2:22])=[CH:17][CH:16]=1>C1C=CC=CC=1.C1COCC1>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:13])[C@:3]12[CH2:22][C@:21]1([C:18]1[CH:17]=[CH:16][C:15]([I:14])=[CH:20][CH:19]=1)[CH:23]([CH3:25])[CH3:24]

참가 물질

5

반응물 2

HCID 672301281-Iodo-4-(2-methyl-1-methylene-propyl)-benzeneHCID 178514325HCID 178514325, 화합물

생성물 1

HCID 58305290(1R,2R)-5'-fluoro-2-(4-iodophenyl)-2-isopropylspiro[cyclopropane-1,3'-indolin]-2'-one수율 105.9%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

The 3-diazo-5-fluoroindolin-2-one (0.177 g, 1 mmol) and Rh(OAc)2 dimer (2.2 mg) were placed into a Schlenk tube under Argon atmosphere, then dissolved in dry benzene (3 mL). The mixture was heated to 80° C. for 10 minutes. The 1-iodo-4-(3-methylbut-1-en-2-yl)benzene (0.544 g) was dissolved in dry THF (2 mL) and added into the mixture in one portion. The mixture was concentrated in vacuo, the residue was purified by flash column chromatography (Petroleum ether: AcOEt=5:1) to give the title compound as white powder (0.446 g, 53%). LC/MS m/e calcd. for C19H17FINO: 421, observed (M+H)+: 422.1.

후처리

  1. additionadded into the mixture in one portion
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash column chromatography (Petroleum ether: AcOEt=5:1)

출처 및 근거

ORD 기록
ord-5f4d20452a4045bfa07ed6c1773935e0
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354443B2

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