Triethylamine → 3-Amino-6-[1-(tert-butoxycarbonyl)indol-2-yl]phthalimide

HRID 20994

Reaktionsgleichung

Reaktionsgleichung von HRID 20994
[NH2:1][C:2]1[CH:12]=[CH:11][C:10](Br)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[C:14]([O:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1B(O)O)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:22]2[N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[C:29]3[C:24]([CH:23]=2)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 684890894-amino-7-bromo-2,3-dihydro-1H-isoindole-1,3-dione

Produkt 1

HCID 684928123-Amino-6-[1-(tert-butoxycarbonyl)indol-2-yl]phthalimideAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Amino-6-bromophthalimide (100 mg, 0.415 mmol) was dissolved in acetonitrile (7 mL), and the solution was added with 1-(tert-butoxycarbonyl)indole-2-boronic acid (217 mg, 0.830 mmol), palladium acetate (7.5 mg, 0.033 mmol), tri(o-tolyl)phosphine (20 mg, 0.066 mmol) and triethylamine (0.578 mL, 4.15 mmol), followed by stirring under reflux for 7.5 hours under argon atmosphere. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1, chloroform/acetonitrile=15/1) to obtain 3-amino-6-[1-(tert-butoxycarbonyl)indol-2-yl]phthalimide (106 mg, yield 67%).

Aufarbeitung

  1. temperatureunder reflux for 7.5 hours under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1, chloroform/acetonitrile=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-9c1c603f370e42a6815d8cd8dc0247c2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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