Diisopropylethylamine → 3-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-alpha]pyridine

HRID 1180222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180222
CCN(C(C)C)C(C)C.FC(F)(F)S([O:15][Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])(=O)=O.[Br:25][C:26]1[N:30]2[CH:31]=[CH:32][C:33]([C:36](O)([CH3:38])[CH3:37])=[C:34]([F:35])[C:29]2=[N:28][CH:27]=1>C(Cl)Cl>[Br:25][C:26]1[N:30]2[CH:31]=[CH:32][C:33]([C:36]([O:15][Si:16]([CH2:17][CH3:18])([CH2:19][CH3:20])[CH2:21][CH3:22])([CH3:38])[CH3:37])=[C:34]([F:35])[C:29]2=[N:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Produkt 1

HCID 695489923-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-alpha]pyridineAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Hünig's base (0.44 ml, 3.8 mmol) and triethylsilyl trifluoromethanesulfonate (0.57 ml, 2.6 mmol) were added sequentially to a cold (−78° C.), stirred solution of 2-(3-bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (637 mg, 2.3 mmol) in CH2Cl2 (13 ml) and the solution warmed to ambient temperature. The mixture was partitioned between CH2Cl2 (50 ml) and water (50 ml) and the organic phase dried over anhydrous MgSO4, filtered through a short plug of silica (eluent CH2Cl2) and concentrated to afford 3-bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-α]pyridine (906 mg, quant.): δH (360 MHz, CDCl3) 0.70 (6H, q, J 7.8), 0.99 (9H, t, J 7.8), 1.71 (6H, s), 7.32 (1H, t, J 6.9), 7.59 (1H, s), 7.88 (1H, d, J 7.3).

Aufarbeitung

  1. customThe mixture was partitioned between CH2Cl2 (50 ml) and water (50 ml)
  2. dry with materialthe organic phase dried over anhydrous MgSO4
  3. filtrationfiltered through a short plug of silica (eluent CH2Cl2)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-efbe2fe973db4c58adc61f645e566020
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279580B2

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