Nitrogen → HCID 69671657, compound
Reaction equation
N#N.Br[C:4]([F:13])([F:12])[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[CH2:14]([Sn](CCCC)(CCCC)CCCC)[CH:15]=[CH2:16].CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[F:12][C:4]([F:13])([CH2:16][CH:15]=[CH2:14])[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-2,2-difluoro-1-(pyrrolidin-1-yl)ethanone (600 mg, 2.63 mmol) in dry toluene (18 mL) was added allyltributyltin (0.84 mL, 2.63 mmol) and AIBN (9 mg, 0.05 mmol) at rt. The reaction mixture was stirred at 100° C. for 1 h. AIBN (9 mg, 0.05 mmol) was then added again and the reaction mixture further stirred at 100° C. for 30 h. The solvent was removed under reduced pressure and the crude residue purified by FC (SiO2 containing 10% KF, hept-EA, 1:0→4:1) to give the title compound as a colorless oil. LC-MS-conditions 08: tR=0.73 min; [M+H]+=190.30.
Workup
- stirringthe reaction mixture further stirred at 100° C. for 30 h
- customThe solvent was removed under reduced pressure
- customthe crude residue purified by FC (SiO2 containing 10% KF, hept-EA, 1:0→4:1)
Sources & evidence
- ORD record
- ord-ee55767f1e8b40009c02be216e1aa863
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187435B2
Reaction notes
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