تفاعل #2388241

معادلة التفاعل

ethyl acetate

Triisopropylsilanethiol

sodium hydride

(R)-N-(2-chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

(R)-N-(2-Chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

→

title compound

(R)-N-(2-Chloro-4-(triisopropylsilylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

المذيبات

THF

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was heated to 85° C. for 2 hours
2. 2
   درجة الحرارةto cool to ambient temperature
3. 3
   غسيلthe mixture as washed with brine (100 ml)
4. 4
   أخرىdried
5. 5
   أخرىVolatile material was removed by evaporation
6. 6
   أخرىthe residue was purified on a silica gel flash column
7. 7
   غسيلeluting with 1-20% ethyl acetate/hexane

الإجراء التجريبي

Triisopropylsilanethiol (2.8 ml) was added to a stirred suspension of sodium hydride (60% mineral oil dispersion, 0.53 g) in anhydrous THF (40 ml) cooled to 0° C. under argon. After 15 minutes at this temperature tetrakis(triphenylphosphine)palladium(0) (1.21 g) was added and this solution was added to (R)-N-(2-chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 197) (5.2 g) in anhydrous toluene (40 ml) and the mixture was heated to 85° C. for 2 hours. The mixture was allowed to cool to ambient temperature. ethyl acetate (200 ml) was added and the mixture as washed with brine (100 ml) and dried. Volatile material was removed by evaporation and the residue was purified on a silica gel flash column eluting with 1-20% ethyl acetate/hexane to give the title compound (6.51 g) as a gum. NMR (CDCl3) 1.07-1.1 (d, 18H), 1.20-1.28 (m, 3H), 1.74 (s, 3H), 3.64 (s, 1H), 7.39-7.42 (m, 1H), 7.53 (s, 1H), 8.23 (d, 1H), 8.81 (s, 1H); MS (ESP−): 454.

المصدر