3-Acetyl-5-bromopyridine → HCID 59250365, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[N:6][CH:7]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4](/[C:8](=[N:17]/[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])/[CH3:9])[CH:5]=[N:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 1-(5-bromopyridin-3-yl)ethanone (1.01 g, 5.04 mmol) in DCM (20 mL) was added (R)-2-methylpropane-2-sulfinamide (0.555 g, 4.58 mmol) followed by Ti(OEt)4 (1.23 g, 4.58 mmol) dropwise and the reaction mixture was heated to 40° C. over night. After cooling, the solvent was removed under vacuum and the residue taken up in EtOAc (80 mL). This solution was vigorously stirred while a saturated solution of brine (20 mL) was slowly added. After 15 min, the mixture was filtered through a plug of Dicalite and washed with EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 50% EtOAc-heptane gradient to give the title compound (0.964 g, 69%) as a yellow oil. MS: 303.1 and 305.0 (M+H+).
Workup
- temperatureAfter cooling
- customthe solvent was removed under vacuum
- additionwas slowly added
- filtrationthe mixture was filtered through a plug of Dicalite
- washwashed with EtOAc
- customThe organic phase was separated
- dry with materialdried over Na2SO4
- customevaporated to dryness
- customThe residue was purified by silica gel flash chromatography
- washeluting with a 0 to 50% EtOAc-heptane gradient
Sources & evidence
- ORD record
- ord-06a4bb450e794ec29c2a23e0c836275d
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260408B2
Reaction notes
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