Sodium hydride → Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate
Reaction equation
[CH3:1][C:2]([O:5][C:6]([CH2:8][OH:9])=[O:7])([CH3:4])[CH3:3].[H-].[Na+].[Br:12][C:13]1[C:14](Cl)=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=1>C1COCC1>[C:2]([O:5][C:6](=[O:7])[CH2:8][O:9][C:14]1[C:13]([Br:12])=[CH:18][C:17]([Cl:19])=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:1]Participants
Procedure
A solution of 2-tert-butyl glycolate (437 mg; 3.31 mmol) in anhydrous THF (5 mL) was treated with NaH (159 mg; 3.97 mmol) and stirred at RT for 10 minutes before treating with a solution of 3-bromo-2,5-dichloropyridine (Matrix; 500 mg; 2.20 mmol) in anhydrous THF (5 mL). The resulting reaction mixture was stirred for 22 hours. The reaction mixture was treated with a solution of 2-tert-butyl glycolate (437 mg; 3.31 mmol) in THF (2 ml), then with NaH (159 mg; 3.97 mmol) and the reaction mixture was stirred for 16 h. The reaction was quenched with tBuOH, the solvent removed under reduced pressure affording a brown solid, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc, affording the title compound as a yellow sticky solid.
Workup
- customThe resulting reaction mixture
- stirringwas stirred for 22 hours
- customThe reaction was quenched with tBuOH
- customthe solvent removed under reduced pressure
- customaffording a brown solid, which
- customwas purified by flash column chromatography (silica)
- washeluting with cyclohexane containing
- temperatureincreasing amounts of EtOAc
Sources & evidence
- ORD record
- ord-6652785368514f6cb8ed87741996c671
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273769B2
Reaction notes
Loading…