Cesium carbonate → HCID 9863473, Verbindung

HRID 1581686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1581686
Br[C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[C:4]([N:6]([CH3:18])[CH2:7][C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:5].[N:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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.COCCOC.O>[CH3:18][N:6]([CH2:7][C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4](=[O:5])[C:3]1[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=1[C:26]1[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 227220782-Bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamide

Produkt 1

HCID 9863473HCID 9863473, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamide (0.30 g, 0.84 mmole), pyridine-4-boronic acid (0.20 g, 1.63 mmole), tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmole), and Cs2CO3 (1.10 g, 3.38 mmole) in 10:1 DME/H2O (25 mL) was degassed, then was heated under N2 overnight. The resulting mixture was concentrated in vacuo, and the residue was taken up in 10% NaOH solution. The mixture was extracted with CH2Cl2, and the combined organic extracts were washed with brine and dried (MgSO4). Flash chromatography on silica gel (3% MeOH/CH2Cl2) followed by preparative TLC (3% MeOH/CH2Cl2) gave the title compound (98 mg, 33%) as a white solid: 1H NMR (300 MHz, CDCl3) indicated an approximately 5:1 mixture of amide rotamers; for the major rotamer: 6 8.50-8.65 (m, 2H), 7.00-7.60 (m, 10H), 6.27 (s, 1H), 4.50-5.00 (m, 2H), 3.62 (s, 3H), 2.49 (s, 3H); for the minor rotamer: δ 8.65-8.75 (m, 2H), 7.00-7.60 (m, 10H), 6.12 (s, 1H), 4.50-5.00 (m, 2H), 3.41 (s, 3H), 2.86 (s, 3H); MS (ES) m/e 356 (M+H)+. Anal. Calcd for C23H21N3O.0.10H2O: C, 77.33; H, 5.98; N, 11.76. Found: C, 77.07; H, 5.98; N, 11.56.

Aufarbeitung

  1. temperaturewas heated under N2 overnight
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-defbbb30fd6943a281f96adf201b7c5d
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06730684B1

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