1,2-Dimethoxyethane → 2-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-6-phenylimidazo[1,2-a]pyridine

HRID 1416299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416299
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1.C(COC)OC.[C:31]1(OB(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>O.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>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:7][N:6]4[CH:8]=3)[CH2:13][CH2:14]2)=[CH:19][CH:20]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 78412Phenyl dihydrogen orthoborateHCID 516892Sodium BicarbonateHCID 193671286-Bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

Produkt 1

HCID 193671002-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-6-phenylimidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine. (Example 23; 0.091 g), tetrakis(triphenylphosphine)palladium (0) (Aldrich; 0.0078 g), and dimethoxyethane (2 mL) is stirred at room temperature for 10 min, at which time phenylboric acid (Aldrich; 0.0306 g) is added, followed by sodium bicarbonate (0.0565 g) in water (1 mL). The mixture is stirred at reflux for 3 h and then allowed to cool. Dimethoxyethane is removed under reduced pressure and the residue is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel using acetone/dichloromethane/methanol (50/200/1) to give 0.027 g of the title compound. MS m/z 402; 1H NMR (CDCl3) δ2.76, 3.21, 3.80, 6.84, 7.19, 7.37-7.58, 7.61, 7.64, 8.26.

Aufarbeitung

  1. additionis added
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. customDimethoxyethane is removed under reduced pressure
  5. customthe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  6. dry with materialThe organic layers are dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d0483329bd6a45cc8e10050c02567012
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912246

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