Methanol → Tert-butyl 3-[4,6-dibromo-2-(2,4-difluorophenyl)pyridin-3-yl]propanoate
Reaction equation
C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].[C:13]([O:17][C:18](=[O:20])[CH3:19])([CH3:16])([CH3:15])[CH3:14].[Br:21][C:22]1[CH:27]=[C:26]([Br:28])[N:25]=[C:24]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])[C:23]=1[CH3:37].CO>C1COCC1>[Br:21][C:22]1[CH:27]=[C:26]([Br:28])[N:25]=[C:24]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])[C:23]=1[CH2:37][CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
To a −78° C. solution of the lithium bis(trimethylsilylamide) (14 mL) in mL of THF was added t-butylacetate (2 mL). After stirring for 10 min, 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine (1.0 g) dissolved in 3 mL THF was added dropwise. The mixture stirred at −78° C. for 1.5 h, then warmed to −50° C. The reaction mixture was then recooled to −78° C. and 3 mL of methanol was added. The solution stirred for 24 h at rt. The crude mixture was purified by flash chromatography, eluting with 50% ethyl acetate/hexanes. Mass spectrum m/z (ESI) 478.3 (M+1).
Workup
- additionwas added dropwise
- stirringThe mixture stirred at −78° C. for 1.5 h
- customwas then recooled to −78° C.
- stirringThe solution stirred for 24 h at rt
- customThe crude mixture was purified by flash chromatography
- washeluting with 50% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-3ca4f266e1b14110a72cf21f59ed7fb8
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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