Reacción #84022

Ecuación de reacción

sodium hydride

N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((3,3,3-trifluoropropyl)thio)propanamide

ethyl bromide

potassium iodide

→

N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide

Disolventes

sulfolane

sulfolane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas slowly added dropwise over 5 minutes
2. 2
   Otroafter 3 minutes
3. 3
   workup.ADDITIONwere added sequentially
4. 4
   workup.STIRRINGto stir at room temperature
5. 5
   OtroThe reaction was quenched after 6 hours
6. 6
   workup.ADDITIONby being poured drop-wise
7. 7
   Temperaturainto cooled ammonium formate/acetonitrile solution (30 mL)
8. 8
   workup.STIRRINGThe resulting orange colored solution was stirred
9. 9
   workup.ADDITIONtetrahydrofuran (40 mL) was added

Procedimiento

To 3-neck round bottomed flask (50 mL) was added sodium hydride (60% in oil, 0.130 g, 3.28 mmol) and sulfolane (16 mL). The gray suspension was stirred for 5 minutes then N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((3,3,3-trifluoropropyl)thio)propanamide (1.20 g, 3.16 mmol) dissolved in sulfolane (25 mL) was slowly added dropwise over 5 minutes. The mixture became a light gray suspension after 3 minutes and was allowed to stir for 5 minutes after which time ethyl bromide (0.800 mL, 10.7 mmol) and potassium iodide (0.120 g, 0.720 mmol) were added sequentially. The cloudy suspension was then allowed to stir at room temperature. The reaction was quenched after 6 hours by being poured drop-wise into cooled ammonium formate/acetonitrile solution (30 mL). The resulting orange colored solution was stirred and tetrahydrofuran (40 mL) was added. The mixture was assayed, using octanophenone as a standard, and found to contain (1.09 g, 85%) of the desired product with a selectivity versus the retro-Michael-like decomposition product of 97:3.

Fuente