Sodium hydride → (3-((5-Bromopyridin-2-yl)oxy)propyl)dimethylamine
Reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[Br:10][C:11]1[CH:12]=[CH:13][C:14](F)=[N:15][CH:16]=1>CN(C=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])=[N:15][CH:16]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
3-(Dimethylamino)propan-1-ol (3.09 g, 29.95 mmol) was added to a mixture of sodium hydride (2.4 g, 60.00 mmol) in DMF (50 mL) over a period of 20 min at r.t. 5-Bromo-2-fluoropyridine (5.81, g, 33.01 mmol) was added and the resulting solution stirred for 4 h at 30° C. The reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride and the resulting mixture concentrated under vacuum. The residue was purified by FCC, eluting with DCM/MeOH in Et2O (10:1) to afford the desired material (5.2 g, 67%) as yellow oil. Mass Spectrum: m/z (ES+)[M+H]+=259.
Workup
- customThe reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride
- concentrationthe resulting mixture concentrated under vacuum
- customThe residue was purified by FCC
- washeluting with DCM/MeOH in Et2O (10:1)
Sources & evidence
- ORD record
- ord-a22812e96914415ba4820f32fd4633e6
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428503B2
Reaction notes
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