Sodium Carbonate → 3-(1-Methyl-1,2,3,4-tetrahydro-pyridin-4-yl)-5-trifluoromethyl-phenylamine
Reaction equation
CC1(C)COB([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)OC1.[CH3:20][N:21]1[CH2:26][CH:25]=[C:24](OS(C(F)(F)F)(=O)=O)[CH2:23][CH2:22]1.[Li+].[Cl-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:20][N:21]1[CH:22]=[CH:23][CH:24]([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[CH2:25][CH2:26]1Participants
Reactant 5
Product 1
Conditions
- Temperature
- 80 °C
Procedure
3-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5-trifluoromethyl-phenylamine (1.2 g) was added to trifluoro-methanesulfonic acid 1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl ester (1.0 g), LiCl (500 mg, Aldrich), PPh3 (300 mg, Aldrich) and 2M Na2CO3 aqueous solution (6 ml) and was bubbled with N2 for 5 min. Pd(PPH3)4 (300 mg, Aldrich) was added and the reaction was heated to 80° C. for 16 h. The reaction was cooled to RT and diluted with Et2O (100 mL). The mixture was filtered through Celite® and the filtrate was washed with NaHCO3 aqueous solution (25 ml) followed by brine (25 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The desired compound was isolated by silica gel column chromatography (EtOAc 10% (2M NH3) in MeOH/EtOAc) to provide yellow oil. M+H 257.2; Calc'd 256.1.
Workup
- customwas bubbled with N2 for 5 min
- additionPd(PPH3)4 (300 mg, Aldrich) was added
- temperatureThe reaction was cooled to RT
- additiondiluted with Et2O (100 mL)
- filtrationThe mixture was filtered through Celite®
- washthe filtrate was washed with NaHCO3 aqueous solution (25 ml)
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-76e0c61cd0344a5c905562f83b93a50d
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247430B2
Reaction notes
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