Triethylamine → 2-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione

HRID 1356286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356286
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:2]1.CCN(CC)CC.C(OCl)(C)(C)C.[CH3:36][C:37]([CH3:49])=[CH:38][CH2:39]B1C2CCCC1CCC2>C1COCC1>[CH3:36][C:37]([C:2]1[NH:1][C:9]2[C:4]([C:3]=1[CH2:10][CH2:11][N:12]1[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]1=[O:21])=[CH:5][CH:6]=[CH:7][CH:8]=2)([CH3:49])[CH:38]=[CH2:39]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2885772-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dioneHCID 521297Tert-Butyl hypochloriteHCID 53261919-(3-Methyl-2-butenyl)-9-bora-bicyclo[3.3.1]nonane

Produkt 1

HCID 223969612-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-[2-(1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione (3.77 g, 13.0 mmol) in dry THF (0.13 L) under argon was added NEt3 (1.84 mL, 13.0 mmol). This mixture was cooled to −78° C., and neat t-BuOCl (1.54 mL, 13.0 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. A solution of 9-(3-methyl-2-butenyl)-9-bora-bicyclo[3.3.1]nonane (40 mmol) in hexanes was added. The reaction mixture was stirred for 6 h at −78° C. It was quenched with 1 M aq HCl, and permitted to warm to rt overnight. The reaction mixture was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to give an oil. The oil was purified by silica chromatography to give the title compound: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 381.2, 359.2; 1H NMR (300 MHz, CDCl3) δ 7.91 (1H), 7.88-7.69 (5H), 7.29 (1H), 7.10 (2H), 6.18 (1H), 5.25 (2H), 3.95 (2H), 3.16 (2H), 1.61 (6H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 6 h at −78° C
  2. customIt was quenched with 1 M aq HCl
  3. temperatureto warm to rt overnight
  4. extractionThe reaction mixture was extracted with CH2Cl2
  5. dry with materialThe CH2Cl2 extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe oil was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4b857730e56240b2ba65abda59e82d85
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586421B2

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