N,N,N',N'-Tetramethylethylenediamine → 2-Chloro-N,N-diethyl-6-(trimethylstannyl)benzamide
Reaction equation
[Li]C(CC)C.C1CCCCC1.[CH2:12]([N:14]([CH2:24][CH3:25])[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])[CH3:13].CN(CCN(C)C)C.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36]>C1COCC1.CCOCC>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Sn:35]([CH3:37])([CH3:36])[CH3:34])[C:16]=1[C:15]([N:14]([CH2:12][CH3:13])[CH2:24][CH3:25])=[O:23]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
1.3M s-BuLi in cyclohexane (4.8 mL, 6.2 mmol) was added dropwise to a −78° C. cooled solution of the compound of Example e (1.0 g, 4.7 mmol) and TMEDA (930 μL, 6.2 mmol) in THF (15 mL). The resulting yellow mixture was stirred at −78° C. for 45 min, then was quenched by the dropwise addition of trimethyltin chloride (1.41 g, 7.1 mmol) in THF (5 mL), maintaining the internal reaction temperature ≦−65° C. The resulting green solution was warmed to RT to afford a yellow solution which was diluted with ether and extracted twice with aq 10% HCl, and once with sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and purified by HPLC with 1:4 ethyl acetate/hexanes to afford 1.37 g of the title compound, an 81% yield, as a colorless oil.
Workup
- temperaturemaintaining the internal reaction temperature ≦−65° C
- temperatureThe resulting green solution was warmed to RT
- customto afford a yellow solution which
- extractionextracted twice with aq 10% HCl
- dry with materialThe ether solution was dried (MgSO4)
- concentrationconcentrated
- custompurified by HPLC with 1:4 ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-d52e8883f86c444989ba79e646556305
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248894B1
Reaction notes
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