Sodium Thiosulfate → 1-(5-Bromothiazol-2-yl)cyclohexanecarbonitrile
Reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14]1([C:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[Br:1][C:13]1[S:9][C:10]([C:14]2([C:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:11][CH:12]=1Participants
Procedure
N-Bromosuccinimide (0.33 g, 1.87 mmol) was added to a solution of the product from Step 1 (300 mg, 1.56 mmol) in DMF (5 ml) and the resulting reaction mixture was stirred at room temperature for 2 hrs. 2 aliquots of N-bromosuccinimide (0.33 g, 1.87 mmol) were added over a period of 23 hrs before addition of saturated aqueous Na2S2O3 (10 mL). The mixture was then extracted with EtOAc (2×20 mL) and the combined organic layers were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (gradient elution 7% to 60% EtOAc in Hexanes) to afford 1-(5-bromo-1,3-thiazol-2-yl)cyclohexanecarbonitrile (96 mg, 0.35 mmol, 22.7% yield) as a pale yellow oil. MS ESI: [M+H]+ m/z 272.
Workup
- customthe resulting reaction mixture
- extractionThe mixture was then extracted with EtOAc (2×20 mL)
- washthe combined organic layers were washed with brine (50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica (gradient elution 7% to 60% EtOAc in Hexanes)
Sources & evidence
- ORD record
- ord-1d20ad8f18d74123853695801bfd05ca
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08551984B2
Reaction notes
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