3-Butyn-1-OL → 4-Chloro-7-[1-(tert-butoxycarbonyl)-3-(4-hydroxy-1-butynyl)indol-2-yl]isoindolinone

HRID 21109

반응식

HRID 21109 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:13]3[C:18]([C:19]=2I)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:28].[CH2:29]([OH:33])[CH2:30][C:31]#[CH:32]>C(NCC)C.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)I>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:13]3[C:18]([C:19]=2[C:32]#[C:31][CH2:30][CH2:29][OH:33])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:28]

참가 물질

6

반응물 2

HCID 135663-Butyn-1-OLHCID 684922044-Chloro-7-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]isoindolinone

생성물 1

HCID 684925324-Chloro-7-[1-(tert-butoxycarbonyl)-3-(4-hydroxy-1-butynyl)indol-2-yl]isoindolinone수율 87%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

In a similar manner to Step 2 of Example 161, 4-chloro-7-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]isoindolinone (148 mg, 0.291 mmol) was dissolved in diethylamine (7.4 mL), and the Solution was treated with bis(triphenylphosphine)dichloropalladium (16.3 mg, 0.0233 mmol), copper iodide (11.1 mg, 0.0582 mmol) and 3-butyn-1-ol (0.220 mL, 2.91 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=10/1) to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-3-(4-hydroxy-1-butynyl)indol-2-yl]isoindolinone (114 mg, yield 87%).

후처리

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=10/1)

출처 및 근거

ORD 기록
ord-821a80924f364c75a54c9d8ed1fed4a8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

연결된 노트

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