N-Methyl dicyclohexylamine → HCID 86685861, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:4][CH:3]=1.[C:16]([O:21][CH2:22][CH3:23])(=[O:20])/[CH:17]=[CH:18]/[CH3:19].C1(N(C)C2CCCCC2)CCCCC1>[Cl-].C([N+](CC)(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(N(C)C)=O>[F:13][C:12]([F:15])([F:14])[CH2:11][CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[C:18](/[CH3:19])=[CH:17]/[C:16]([O:21][CH2:22][CH3:23])=[O:20])=[CH:3][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
Intermediate 11A (2.81 g, 9.93 mmol), (E)-ethyl but-2-enoate (1.25 g, 10.9 mmol), palladium(II) acetate (0.11 g, 0.5 mmol), tetraethylammonium chloride (1.65 g, 9.9 mmol), N-cyclohexyl-N-methylcyclohexanamine (2.91 g, 14.9 mmol) and dimethylacetamide (30 ml) were placed in a oven-dried vial and sparged with argon for 5 min. The vial was sealed and the reaction heated to 110° C. for 6 h. The reaction was cooled to rt, diluted with EtOAc (75 mL), washed with water and sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with EtOAc in hexanes to provide Intermediate 11B (1.81 g, 49%) as a colorless oil. LCMS Anal. Calc'd for C16H19F3O3 316.32, found [M+H] 317.2.
Workup
- customsparged with argon for 5 min
- customThe vial was sealed
- temperatureThe reaction was cooled to rt
- additiondiluted with EtOAc (75 mL)
- washwashed with water
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
- washeluting with EtOAc in hexanes
Sources & evidence
- ORD record
- ord-590696793d6946d0802d8f78f838db30
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791091B2
Reaction notes
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