Methanesulfonic Acid → 2-Isopropyl-3-(2,2,2-trifluoroethoxy)pyridine
Reaction equation
N[C:2]1[C:3](SC(C)C)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].CS(O)(=O)=O.[C:23](ON=O)(C)([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>>[CH:23]([C:3]1[C:2]([O:15][CH2:14][C:13]([F:17])([F:16])[F:12])=[CH:7][CH:6]=[CH:5][N:4]=1)([CH3:25])[CH3:24]Participants
6
Procedure
A reactor vessel is charged with 3-amino-2-isopropylthiopyridine (3.0 g, 18 mmol), 2,2,2-trifluoroethanol (21 g, 210 mmol), and methanesulfonic acid (1.7 g, 18 mmol). The solution is heated to the range 65° C. to 70° C. and then t-butylnitrite (2.2 g of a 90% solution, 19 mmol) is added drop-wise to the vessel while maintaining the temperature at 65° C. to 70° C. After nitrogen evolution ceases, the solution is cooled, neutralized with aqueous saturated sodium bicarbonate solution and then extracted with MTBE. The solvent is removed by evaporation to obtain 2-isopropyl-3-(2,2,2-trifluoroethoxy)pyridine as a crude oil (4.22 g, crude yield 94%).
Workup
- temperatureThe solution is heated to the range 65° C. to 70° C.
- temperaturewhile maintaining the temperature at 65° C. to 70° C
- temperatureAfter nitrogen evolution ceases, the solution is cooled
- extractionextracted with MTBE
- customThe solvent is removed by evaporation
Sources & evidence
- ORD record
- ord-80543af066384dcbad32e639f945787c
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06710180B2
Reaction notes
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