2-Bromopyridine → HCID 67981349, compound
Reaction equation
[C:1]12([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:9][CH:8]=3)[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.CCN(C(C)C)C(C)C.Br[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1>C(Cl)Cl.O>[O:23]=[C:14]1[N:13]([C:10]2[CH:9]=[CH:8][C:7]([C:1]34[CH2:6][CH:5]3[CH2:4][N:3]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[CH2:2]4)=[CH:12][CH:11]=2)[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (0.4 g, 1.1 mmol) in DCM (5 mL) were added DIPEA (0.5 mL, 3.4 mmol) and 2-bromopyridine (0.9 mL, 5.7 mmol) at r.t. The reaction mixture was stirred at 90° C. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with water (10 mL) and extracted with DCM (2×20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3) to provide the title compound (0.3 g, 67%) as white solid.
Workup
- extractionextracted with DCM (2×20 mL)
- washThe organic layer was washed with brine (10 mL)
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated in vacuo
- customThe crude was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3)
Sources & evidence
- ORD record
- ord-500dcfff3a8b4ff7a6ecda365dd20fe3
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906913B2
Reaction notes
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