Imidazole → 5-[3-(tert-Butyl-dimethyl-silanoxy)-propyl]-2'-trifluoromethyl-biphenyl-3,4-diamine

HRID 1518130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518130
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][OH:22].N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C(Cl)Cl>[C:29]([Si:32]([CH3:34])([CH3:33])[O:22][CH2:21][CH2:20][CH2:19][C:3]1[C:2]([NH2:1])=[C:7]([NH2:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:16])([F:17])[F:18])[CH:4]=1)([CH3:31])([CH3:30])[CH3:28]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 592800973-(4,5-Diamino-2'-trifluoromethyl-biphenyl-3-yl)-propan-1-ol

Produkt 1

HCID 592801095-[3-(tert-Butyl-dimethyl-silanoxy)-propyl]-2'-trifluoromethyl-biphenyl-3,4-diamineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(4,5-Diamino-2′-trifluoromethyl-biphenyl-3-yl)-propan-1-ol (101 mg, 0.324 mmol, as prepared in the previous step) was placed in an 8 mL vial equipped with a magnetic stir bar, and DCM (2 mL) was added via pipette. Imidazole (1.1 eq., 24.5 mg, 0.356 mmol) and TBSCl (1.1 eq., 53.7 mg, 0.356 mmol) were added sequentially as solids, and the reaction was stirred at RT for 2 h. The reaction was filtered, the precipitate was washed once with DCM (5 mL), and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography on a 24-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0:1 to 1:1, v/v over 30 min, yielding 93.2 mg (68%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.69 (d, J=7.8 Hz, 1H), 7.49 (t, J=7.5 Hz, 1H), 7.38 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.61 (s, 1H), 6.59 (s, 1H), 3.66 (t, J=5.9 Hz, 2H), 3.52 (br. s., 4H), 2.65 (t, J=7.3 Hz, 2H), 1.75-1.87 (m, 2H), 0.91 (s, 9H), 0.07 (s, 6H).

Aufarbeitung

  1. customvial equipped with a magnetic stir bar
  2. filtrationThe reaction was filtered
  3. washthe precipitate was washed once with DCM (5 mL)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on a 24-g SiO2 pre-packed column
  6. washeluting with EtOAc/hexanes, 0:1 to 1:1, v/v over 30 min

Quellen und Nachweise

ORD-Eintrag
ord-06051f999f904a6694f8ed025ea663b4
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232409B2

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