Sodium Carbonate → 3,7-Bis-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

HRID 348036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348036
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10](I)=[C:6]2[N:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.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:19][C:20]1[CH:25]=[CH:24][C:23]([C:10]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:8][N:7]3[C:2]([C:16]4[CH:15]=[CH:14][C:13]([Cl:18])=[CH:12][CH:17]=4)=[CH:3][CH:4]=[N:5][C:6]=23)=[CH:22][CH:21]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 21083717HCID 21083717, Verbindung

Produkt 1

HCID 104339283,7-Bis-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
72 °C

Versuchsvorschrift

A mixture of 7-chloro-2-(2-chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidine (I-1A-1d; 50 mg, 0.13 mmol), 4-chlorophenylboronic acid (30 mg, 0.19 mmol), Na2CO3 (108 mg, 0.67 mmol), and tetrakis(triphenylphosphine)palladium (15 mg, 0.013 mmol) in ethanol (1 ml) and water (0.23 ml) was degassed (3×) by pulling a vacuum followed by refilling with nitrogen gas. The reaction was heated at 72° C. for 2 hr, cooled to room temperature, and then extracted from water with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo. Purification on a Chromatotron using 20% ethyl acetate in hexanes as eluant afforded compound 14A-1 (17 mg, 30%) as a solid: +ESI MS (M+1) 450.3; 1H NMR (400 MHz, CD2Cl2) δ 8.62 (d, J=4.1 Hz, 1H), 8.01 (d, J=8.7 Hz, 2H), 7.56 (d, J=8.7 Hz, 2H), 7.51–7.36 (m, 6H), 7.28 (d, J=8.7 Hz, 2H), 7.04 (d, J=4.1 Hz, 1H).

Aufarbeitung

  1. customwas degassed (3×)
  2. temperaturecooled to room temperature
  3. extractionextracted from water with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated, in vacuo
  7. customPurification on a Chromatotron
  8. customafforded compound 14A-1 (17 mg, 30%) as a solid

Quellen und Nachweise

ORD-Eintrag
ord-ad6bbbad1a24430387cf18f1bec5ada1
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176210B2

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