1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66644050, compound
Reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([O:16][CH3:17])[C:9]=1[Cl:18])(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:18][C:9]1[C:10]([O:16][CH3:17])=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:8]=1[CH:7]=[CH2:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
A solution of 2-(2-chloro-4-cyano-3-methoxyphenyl)ethyl methanesulfonate (207 mg, 0.714 mmol) in DCM (4 mL) was treated with DBU (0.538 mL, 3.57 mmol) and stirred overnight at 40° C. TLC (50% ethyl acetate/hexanes) showed complete conversion to a faster intense UV band for product. The reaction was then diluted with DCM and aq. citric acid and the mixture was extracted twice with DCM. The organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography (5-20% ethyl acetate/hexanes) afforded the title intermediate.
Workup
- extractionthe mixture was extracted twice with DCM
- washThe organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customPurification of the residue by flash chromatography (5-20% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-46c41a4171ce411fa6d6d34540f9f57a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673920B2
Reaction notes
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