Trimethyl borate → 8,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

HRID 2277349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277349
Br[C:2]1[CH:3]=[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]2([CH3:23])[CH3:22])[CH:15]=1.C([Li])CCC.[B:29](OC)([O:32]C)[O:30]C>C1COCC1.C1CCCCC1>[CH3:22][C:5]1([CH3:23])[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=3)[CH:15]=[C:2]([B:29]([OH:32])[OH:30])[CH:3]=2

Komponenten

6

Edukt 3

HCID 8470Trimethyl borateHCID 671097356-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridineHCID 178418339Butyllithium

Produkt 1

HCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

93.7 g (259 mmol) of 6-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine are dissolved in 1500 ml of dry THF, 135 ml (337 mmol) of a 2.5 M solution of n-butyllithium in cyclohexane are added dropwise at −70° C., after 1 h 37 ml of trimethyl borate (336 mmol) are added dropwise, the mixture is warmed to room temperature over the course of 1 h, the solvent is removed, and the residue, which is uniform according to 1H-NMR, is employed in the subsequent reaction without further purification.

Aufarbeitung

  1. additionare added dropwise
  2. customthe solvent is removed
  3. customis employed in the subsequent reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b811b8c28ad6423b8fe72bc2ee85c13d
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133119B2

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