Triphenylphosphine → N-trifluoroacetyl-7-methoxy4-methyl-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine
Reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH:6]([CH3:17])[CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1I)=[O:4].CC([O-])=O.[K+].[CH:25]1[CH:30]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:26]=1>CN(C)C=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:30][C:25](=[CH2:26])[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH:6]1[CH3:17])=[O:4]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A solution of N-allyl, N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine (4.45 g, 10.8 mmol) in dimethylformamide (120 mL) was treated with KOAc (3.17 g, 32.3 mmol), n-Bu4NBr (3.47 g, 10.8 mmol), PPh3 (0.283 g, 1.08 mmol), Pd(OAc)2 (0.242 g, 1.08 mmol) and stirred overnight at 80° C. The product mixture was cooled to 20° C., filtered, diluted with water (200 mL), extracted with ether (3×200 mL), the combined organic phases washed with water (100 mL), brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (10% EtOAc in hexane, silica) resulted in 1.39 g of a yellow oil.
Workup
- temperatureThe product mixture was cooled to 20° C.
- filtrationfiltered
- additiondiluted with water (200 mL)
- extractionextracted with ether (3×200 mL)
- washthe combined organic phases washed with water (100 mL), brine (100 mL)
- dry with materialdried with Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3992f9b6da074349b1e7606574337031
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546378B2
Reaction notes
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