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Sodium Carbonate → 2-(9,9-dimethyl-9H-fluoren-2-yl)-1-methyl-4-(5-methylthiophen-2-yl)-1H-imidazole

HRID 1429116
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Reaktionsgleichung

Reaktionsgleichung von HRID 1429116
I[C:2]1[N:3]([CH3:13])[CH:4]=[C:5]([C:7]2[S:8][C:9]([CH3:12])=[CH:10][CH:11]=2)[N:6]=1.[CH3:14][C:15]1([CH3:31])[C:27]2[CH:26]=[C:25](B(O)O)[CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2.C([O-])([O-])=O.[Na+].[Na+]>O.CN(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>[CH3:14][C:15]1([CH3:31])[C:16]2[CH:17]=[C:18]([C:2]3[N:3]([CH3:13])[CH:4]=[C:5]([C:7]4[S:8][C:9]([CH3:12])=[CH:10][CH:11]=4)[N:6]=3)[CH:19]=[CH:20][C:21]=2[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2
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Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 22348454(9,9-Dimethyl-9H-fluoren-2-yl)boronic acidHCID 675118002-Iodo-1-methyl-4-(5-methylthiophen-2-yl)-1H-imidazole

Produkt 1

HCID 675112242-(9,9-dimethyl-9H-fluoren-2-yl)-1-methyl-4-(5-methylthiophen-2-yl)-1H-imidazoleAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-iodo-1-methyl-4-(5-methylthiophen-2-yl)-1H-imidazole 6 (1.26 g, 4.16 mmol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (1.19 g, 5.00 mmol), Na2CO3 (2.20 g, 20.8 mmol) in H2O (10 mL) and DMF (40 mL) was degassed (N2 bubbling). Pd(PPh3)4 (120 mg, 0.10 mmol) was added and the mixture was heated to reflux for 2 h. The mixture was allowed to cool to room temperature and concentrated. The mixture was filtered through Celite washing with CH2Cl2 and the combined filtrate and washings were concentrated. The residue was taken up in CH2Cl2 and H2O and the organic phase was separated. The aqueous phase was re-extracted (CH2Cl2) and the combined organics were washed (saturated aqueous NaCl), dried (MgSO4), filtered and concentrated to give a residue. The residue was purified by flash chromatography (EtOAc/hexanes 5:95 then 10:90 then 12:88) to give 2-(9,9-dimethyl-9H-fluoren-2-yl)-1-methyl-4-(5-methylthiophen-2-yl)-1H-imidazole 9 (1.19 g, 76%) as a colourless solid. A portion of this material was further purified by, firstly, recrystallisation (EtOAc/hexanes) and, secondly, by sublimation (180° C., 10−6 mBar): m.p. 188-191° C. (DSC)1H NMR (CDCl3, 400 MHz) δ1.53 (s, 6H), 2.50 (d, J=0.6 Hz, 3H), 3.76 (s, 3H), 6.68-6.71 (m, 1H), 7.11 (s, 1H), 7.13-7.19 (m, 1H), 7.32-7.40 (m, 2H), 7.43-7.49 (m, 1H), 7.58 (dd, J 1.4, 8.0 Hz, 1H), 7.73-7.81 (m, 3H); 13C NMR (CDCl3, 100 MHz) δ15.3, 27.1, 34.6, 47.0, 117.1, 119.8, 120.3, 122.1, 122.7, 123.6, 125.6, 127.0, 127.7, 137.8, 138.5, 139.9, 148.3, 153.9, 154.0; HRMS (EI) m/z 370.1490 C24H22N2S [M]+. requires 370.1498.

Aufarbeitung

  1. customwas degassed (N2 bubbling)
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 h
  4. concentrationconcentrated
  5. filtrationThe mixture was filtered through Celite
  6. washwashing with CH2Cl2
  7. concentrationthe combined filtrate and washings were concentrated
  8. customH2O and the organic phase was separated
  9. extractionThe aqueous phase was re-extracted (CH2Cl2)
  10. washthe combined organics were washed (saturated aqueous NaCl)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto give a residue
  15. customThe residue was purified by flash chromatography (EtOAc/hexanes 5:95

Quellen und Nachweise

ORD-Eintrag
ord-79803d8eb2994cfba793b58e243889ed
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08937303B2

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