1,4-Dioxane → 2-{4-[(3,4-Dichlorophenyl)sulfonyl]piperidin-1-yl}-3-(trifluoromethyl)pyridine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:19]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][N:20]=1.CCN(C(C)C)C(C)C.O1CCOCC1>[NH4+].[Cl-].CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:19]3[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 200 °C
Procedure
A mixture of the amine from Step 7D (200 mg, 0.68 mmol), 2-chloro-3-(trifluoromethyl)pyridine (200 mg, 1.36 mmol), DIEA (0.36 mL, 2.04 mmol), and 1,4-dioxane (0.10 mL) was heated in the Emrys Creator microwave to 200° C. for 1 h. The mixture was diluted with sat. NH4Cl (20 mL) and EtOAc (50 mL). The organic phase washed with 10% HCl (25 mL), H2O (3×25 mL), and brine (25 mL), dried (MgSO4), and concentrated. The resulting yellow oil was purified by SiO2 chromatography (elution with 10 to 30% EtOAc-hexanes), and lyophilized to afford the title compound (0.19 g), a white solid, 64%.
Workup
- washThe organic phase washed with 10% HCl (25 mL), H2O (3×25 mL), and brine (25 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe resulting yellow oil was purified by SiO2 chromatography (elution with 10 to 30% EtOAc-hexanes)
Sources & evidence
- ORD record
- ord-eaaf142ac60d4b0a9f1b2e32902baddb
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632838B2
Reaction notes
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