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 1805309ノート

反応式

HRID 1805309 の反応式
[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]

参加物

5

反応物 2

HCID 672301281-Iodo-4-(2-methyl-1-methylene-propyl)-benzeneHCID 178514325HCID 178514325、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5f4d20452a4045bfa07ed6c1773935e0
出典データセット
uspto-grants-2013_01
特許番号
US08354443B2

反応ノート

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