Potassium Carbonate → HCID 22396766, Verbindung

HRID 1356219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356219
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15](Br)[C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCOC(C)=O.CCCCCCC>O1CCCC1.CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 21899848Ethylacetate heptaneHCID 22396782HCID 22396782, Verbindung

Produkt 1

HCID 22396766HCID 22396766, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of 3-benzoyl-7-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.517 g, 1.40 mmol), potassium carbonate (0.77 g, 5.60 mmol), phenylboronic acid (0.194 g, 1.54 mmol), tetrakis(triphenylphosphine)palladium (0.16 g, 0.14 mmol) in tetrahydrofuran (7.0 mL) and N,N-dimethylacetamide (7.0 mL) was stirred at room temperature overnight. The mixture was filtered through Celite and the filtrate concentrated in vacuo to give an oil, which was subjected to column chromatography (silica gel, 10-50% EtOAc/heptane) to afford 0.44 g (86%) of the title compound as a solid: mp 198-200° C.; 1H NMR (400 MHz, CDCl3) δ 8.10, 7.67-7.60, 7.55-7.4, 7.47-7.33, 7.18-7.14, 4.04-3.96, 3.72-3.63, 3.20-3.12, 2.93-2.80; IR (drift) 3258, 1602, 1464, 1430, 1327, 1295, 1239, 1185, 930, 761, 749, 740, 711, 703, 696 cm−1; MS (El) m/z 366 (M+); HRMS (FAB) calcd for C25H22N2O+H: 367.1810, found: 367.1805; Anal. Calcd. for C25H22N20: C, 81.94; H, 6.05; N, 7.64. Found: C, 81.37; H, 6.12; N, 7.57.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give an oil, which

Quellen und Nachweise

ORD-Eintrag
ord-9b602d7f541245629c5a236539920095
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586421B2

Notizen zur Reaktion

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