Sodium Carbonate → HCID 67997101, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[SH:8].Br[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 3-bromopyridine-4-thiol (step A, 4.75 g, 25 mmol), ethyl 2-bromoisobutyrate (9.75 g, 50 mmol), and sodium carbonate (7.95 g, 75 mmol) in DMF (50 mL) was stirred at 60° C. for 1 hour. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was washed with water (2×100 mL) and saturated sodium chloride (100 mL). The aqueous washes were back extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate, concentrated, and purified by normal phase chromatography (a gradient of 0-25% ethyl acetate in hexane) to yield ethyl 2-(3-bromopyridin-4-ylthio)-2-methylpropanoate as a pale yellow oil (6.6 g, 88%).
Workup
- customThe reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL)
- washThe organic layer was washed with water (2×100 mL) and saturated sodium chloride (100 mL)
- extractionThe aqueous washes were back extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
- custompurified by normal phase chromatography (a gradient of 0-25% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-3c7ac6e252394783b61fd703cdb00c62
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541589B2
Reaction notes
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