Iodoethane → Ethyl 2,3-dichloropyridine-4-carboxylate
Reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].I[CH2:15][CH3:16]>CN(C=O)C>[CH2:15]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][N:10]=[C:2]([Cl:1])[C:3]=1[Cl:11])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,3-dichloroisonicotinic acid (5.62 mmol) in 15 mL DMF were added NaH (7.31 mmol) followed by iodoethane (6.75 mmol) at 0° C. The cooling bath was removed and the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (6/4) gives the desired product as yellow oil;
Workup
- customThe cooling bath was removed
- customThe reaction was quenched with sat. aq. NaHCO3 solution
- extractionextracted with EtOAc
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
- customPurification by CC (KP-SIL™ from Biotage)
Sources & evidence
- ORD record
- ord-ccf9cfeb327a4e019818146ffd1f8e6d
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221832B2
Reaction notes
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