2,2'-Bipyridine → 2-Trifluoromethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester
Reaction equation
C(O[C:4](=O)[CH2:5][N:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)C.N1C=CC=CC=1C1C=CC=CN=1.[F-].[K+].C[Si]([C:38]([F:41])([F:40])[F:39])(C)C>CN(C=O)C.[Cu]I.CN1C(=O)CCC1>[CH2:17]([O:16][C:14]([N:6]1[CH2:5][CH2:4][C:13]2[CH:12]=[C:11]([C:38]([F:41])([F:40])[F:39])[S:10][C:9]=2[CH2:8][CH2:7]1)=[O:15])[CH3:18]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A solution of the product from step a.) (75 mg, 0.21 mmol) in DMF (0.5 ml) and NMP (0.5 ml) was treated with bipyridyl (43 mg, 0.27 mmol), CuI (44 mg, 0.23 mmol), KF (13 mg, 0.23 mmol) and trimethylsilyltrifluoromethane (2.1 ml, 1.05 mmol). The reaction mixture was heated to 80° C. for 3 days. The reaction was cooled and filtered through celite washing with EtOAc (20 ml). The eluent was washed with brine (2×3 ml) and dried (MgSO4) providing the subtitle compound as a brown oil that was used without further purification.
Workup
- temperatureThe reaction was cooled
- filtrationfiltered
- washthrough celite washing with EtOAc (20 ml)
- washThe eluent was washed with brine (2×3 ml)
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-2bdb7c26d0cb4058bb29788725dfe7de
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718647B2
Reaction notes
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