2-Bromopyridine → (S)-tert-butyl 2-methyl-4-(pyridin-2-yl)piperazine-1-carboxylate
Reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.CCN(C(C)C)C(C)C>CS(C)=O>[CH3:1][C@H:2]1[CH2:7][N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
To a solution of tert-butyl (2S)-2-methylpiperazine-1-carboxylate (8 g, 39.94 mmol) in DMSO (25 ml) was added 2-bromopyridine (6.594 g, 41.74 mmol), and DIEA (15.48 g, 119.78 mmol). After stirring 2 days at 120° C., the resulting solution was quenched by the addition of DCM (200 ml), washed with water (3×300 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified via silica gel chromatography (3% ethyl acetate in petroleum ether) to afford (S)-tert-butyl 2-methyl-4-(pyridin-2-yl)piperazine-1-carboxylate as a red oil (5.2 g, 47%).
Workup
- customthe resulting solution was quenched by the addition of DCM (200 ml)
- washwashed with water (3×300 ml)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto afford a residue, which
- customwas purified via silica gel chromatography (3% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-0eca1fcfc8ac4cda9fac2206d9eefbd9
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912188B2
Reaction notes
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