Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=O)[C:10]([F:13])([F:12])[F:11].[F:15][C:16]([F:27])([F:26])[C:17](=O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CCCC)CCCC)CCC>CN(C=O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:17]([C:16]([F:26])([F:27])[F:15])[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:9]2[C:10]([F:13])([F:12])[F:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A yellow solution of 1-(2-amino-5-bromophenyl)-2,2,2-trifluoroethanone (1.32 g, 4.94 mmol, Intermediate 8, step b) and 1,1,1-trifluoro-3-phenylpropan-2-one (0.980 g, 5.21 mmol) in DMF (4.95 mL) was treated with tributylamine (1.23 mL, 5.19 mmol) and stirred at 130° C. under air (capped) for 2 hours. The homogeneous orange solution was then cooled to room temperature and partitioned with ether (8 mL) and 1 M NaH2PO4 (8 mL). The organic layer was washed with 1 M NaH2PO4 (1×8 mL), dried (Na2SO4), filtered, and concentrated, and the residue was flash chromatographed with a heptane to 30% DCM/heptane gradient to yield the title compound as a nearly colorless oil.
Workup
- temperatureThe homogeneous orange solution was then cooled to room temperature
- custompartitioned with ether (8 mL) and 1 M NaH2PO4 (8 mL)
- washThe organic layer was washed with 1 M NaH2PO4 (1×8 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customchromatographed with a heptane to 30% DCM/heptane gradient
Sources & evidence
- ORD record
- ord-915754f82def47ea8de6a7901ec31cee
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309222B2
Linked notes
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