Reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15](O)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[CH3:20][N:21]1[C:25]([Sn](CCCC)(CCCC)CCCC)=[CH:24][CH:23]=[N:22]1.[Li+].[Cl-]>CN(C)C=O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([C:25]3[N:21]([CH3:20])[N:22]=[CH:23][CH:24]=3)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of N-trifluoroacetyl-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, O-trifluoromethanesulfonate (100 mg, 0.25 mmol) in dimethylformamide (2 mL) was treated with (2-methyl-2H-pyrazol-3-yl)-tri-n-butyltin (138 mg, 0.37 mmol), LiCl (21 mg, 0.50 mmol), Pd(PPh3)2Cl2 (35 mg, 0.05 mmol) and stirred at 100 C for 4 hours. The product mixture was diluted with EtOAc (20 mL), washed twice with water (10 mL), once with brine (10 mL), dried with Na2SO4 and concentrated. Flash chromatography (30% EtOAc in hexane, silica) resulted in 80 mg of a clear oil. MS calculated for C12H18F3N3O+H: 338, observed: 338.
Workup
- washwashed twice with water (10 mL), once with brine (10 mL)
- dry with materialdried with Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e6a32e9ab0494be9990478a5e03a77b8
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207158B2
Linked notes
Loading…