Diethylamine → HCID 18794751, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](C#C)([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.[CH2:25](NCC)[CH3:26]>[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([F:14])[CH2:12][CH:13]1[C:25]#[C:26][C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
A mixture of 1-tert-butoxycarbonyl-4-ethynyl-4-fluoropiperidine (1 g, 4.4 mmol) and 4-fluoroiodobenzene (610 μl, 5.3 mmol) in N,N-diethylamine (20 ml) was flushed with nitrogen for 15 mins, then palladium bis(tiphenylphosphine)chloride (150 mg, 0.2 mmol) and copper (I) iodide (42 mg, 0.2 mmol) added. The mixture was stirred at room temperature under an atmosphere of nitrogen for 2 hours, then evaporated. The residue was treated with water (50 ml) and extracted with diethyl ether (3×25 ml). The combined organic solutions were washed with water (1×50 ml), brine (1×20 ml), dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, ethyl acetate-hexane 1:9) gave 1.3 g (80%) of the title compound: δH (360 MHz, CDCl3) 1.47 (9H, s), 2.01-2.08 (4H, m), 3.51-3.64 (4H, m), 7.00-7.05 (2H, m), 7.42-7.46 (2H, m).
Workup
- customwas flushed with nitrogen for 15 mins
- customevaporated
- additionThe residue was treated with water (50 ml)
- extractionextracted with diethyl ether (3×25 ml)
- washThe combined organic solutions were washed with water (1×50 ml), brine (1×20 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-65cb89713c75430597d110e8ec7c0bb7
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06048878
Reaction notes
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