تفاعل #1149553

معادلة التفاعل

Caesium fluoride

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

Ethyl acetate

3-bromo-5-carboethoxypyridine

→

title compound

المردود 53.0%

(R)-N-{2-Chloro-4-([5-ethoxycarbonyl-3-pyridyl]sulphanyl)phenyl}-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

المردود 53.0%

المذيبات

DMA

brine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   درجة الحرارةto cool to ambient temperature
3. 3
   ترشيحthe mixture was filtered through a pad of diatomaceous earth which
4. 4
   غسيلwas washed with ethyl acetate (3×50 ml)
5. 5
   غسيلwashed with brine (3×50 ml)
6. 6
   أخرىdried
7. 7
   أخرىVolatile material was removed by evaporation
8. 8
   أخرىthe residue was purified on a silica gel Mega Bond Elut column
9. 9
   غسيلeluting with 10-40% ethyl acetate/iso-hexane

الإجراء التجريبي

Caesium fluoride (0.26 g) was added to a solution of (R)-N-(2-chloro-4-(triisopropylsilylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (0.74 g) (Method 28) in anhydrous DMA (5 ml) under argon and the mixture was stirred for 17 hours. Copper(I) chloride (0.17 g) followed by 3-bromo-5-carboethoxypyridine (0.37 g) were added and the mixture was heated to 155° C. for 4 hours and allowed to cool to ambient temperature. Ethyl acetate (20 ml) and brine (20 ml) were added and the mixture was filtered through a pad of diatomaceous earth which was washed with ethyl acetate (3×50 ml). The filtrates were combined, washed with brine (3×50 ml) and then dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column eluting with 10-40% ethyl acetate/iso-hexane to give the title compound (in 53% yield) as a foam. NMR (CDCl3): 1.39 (t, 3H), 1.57 (s, 3H), 4.00 (s, 1H), 4.40 (q, 2H), 7.34-7.37 (m, 1H), 7.46 (d, 1H), 8.18 (s, 1H), 8.42 (d, 1H), 8.62 (s, 1H), 9.03 (s, 1H), 9.04 (s, 1H); MS (ESP−): 447.

المصدر