Diisopropylethylamine → 3-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-alpha]pyridine
Reaction equation
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- customThe mixture was partitioned between CH2Cl2 (50 ml) and water (50 ml)
- dry with materialthe organic phase dried over anhydrous MgSO4
- filtrationfiltered through a short plug of silica (eluent CH2Cl2)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-efbe2fe973db4c58adc61f645e566020
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279580B2
Reaction notes
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