2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-[6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy-N,N-dimethylpropan-1-amine
Reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[N:11][C:12]=1[F:13].C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>CCCCCC.C1COCC1>[F:13][C:12]1[N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH:9]=[CH:8][C:7]=1[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of n-butyllithium (0.693 g, 10.83 mmol) in n-hexane (4.33 mL) was added to a stirred mixture of 3-(5-bromo-6-fluoropyridin-2-yl)oxy-N,N-dimethylpropan-1-amine (2 g, 7.22 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.014 g, 10.83 mmol) in THF (20 mL) at −78° C. over a period of 20 minutes under an inert atmosphere. The resulting mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with sat. NaHCO3 solution and concentrated in vacuo. The crude product was purified by FCC, elution gradient 0 to 10% MeOH in DCM, to afford the desired material (2.50 g, 1.07%). Mass Spectrum: m/z (ES+)[M+H]+=325.
Workup
- customThe reaction mixture was quenched with sat. NaHCO3 solution
- concentrationconcentrated in vacuo
- customThe crude product was purified by FCC, elution gradient 0 to 10% MeOH in DCM
Sources & evidence
- ORD record
- ord-ddd15e0123ad4e6b9c936d6f3bb80fb5
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428503B2
Reaction notes
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