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

HRID 21109
Notes
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Reaction equation

HRID 21109 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8021DiethylamineSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-821a80924f364c75a54c9d8ed1fed4a8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745641B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes