Triphenylphosphine → N-trifluoroacetyl-7-methoxy4-methyl-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine
Reaction equation
[CH2:1]([N:4]([CH:11]([CH3:22])[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1I)[C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])[CH:2]=[CH2:3].CC([O-])=O.[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C)C=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2]>[F:7][C:6]([F:9])([F:8])[C:5]([N:4]1[CH2:1][C:2](=[CH2:3])[C:14]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=2[CH2:12][CH:11]1[CH3:22])=[O:10]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
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-2c3371b2147845f7a6493f728934cdd7
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514422B2
Reaction notes
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