Toluene → HCID 86670311, compound
Reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1>[F:17][C:16]([F:18])([F:19])[C:15]([C:12]1[CH:11]=[CH:10][C:9]([N:6]2[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]2)=[CH:14][CH:13]=1)([OH:24])[C:20]([F:21])([F:23])[F:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A 20 mL vial was charged with (R)-2-methylpiperazine (0.357 g, 3.56 mmol, Sigma-Aldrich, St. Louis, Mo.), 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.00 g, 3.10 mmol, Bioorg. Med. Chem. Lett. 2002, 12, 3009), sodium tert-butoxide (0.625 g, 6.50 mmol) and 6 mL of toluene. To this was added dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (RuPhos) (0.022 g, 0.046 mmol, Strem Chemical Inc, Newburyport, Mass.), tris(dibenzylideneacetone)dipalladium (0) (0.014 g, 0.015 mmol, Strem Chemical Inc, Newburyport, Mass.). The vial was sealed in heated at 100° C. for 12 h. After that time, the mixture was diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined extracts were dried (MgSO4) and concentrated to give 1,1,1,3,3,3-hexafluoro-2-(4-((3R)-3-methyl-1-piperazinyl)phenyl)-2-propanol (0.950 g) as an oil which was used without purification.
Workup
- customThe vial was sealed
- extractionextracted with EtOAc (2×50 mL)
- dry with materialThe combined extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a866308cbfa9460b8c039d890f55146d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
Loading…