반응 #47853

반응 방정식

5-Bromo-N-tert-butylthiophene-2-carboxamide

N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

cesium fluoride

1,4-dioxane

→

N-tert-butyl-5-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide

수율 59.1%

용매

EtOAc

water

반응 조건

후처리

1. 1
   여과filtered through Celite
2. 2
   세척the Celite was washed with DCM
3. 3
   기타The combined organic solutions were evaporated under reduced pressure
4. 4
   세척washed with saturated sodium bicarbonate
5. 5
   건조dried over MgSO4
6. 6
   기타The organic solutions were evaporated under reduced pressure
7. 7
   기타chromatographed through a Redi-Sep pre-packed silica gel column (40 g)
8. 8
   세척eluting with a gradient of 5% to 95% MeOH in DCM

실험 절차

A 15 ml glass microwave reaction vessel was charged with 5-Bromo-N-tert-butylthiophene-2-carboxamide (1.5 g, 5.7 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (1.7 g, 5.7 mmol), cesium fluoride (0.63 g, 17 mmol), tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.40 mmol), 1,4-dioxane (4 ml, 57 mmol) and water (4 ml). The reaction mixture was heated in a Smith Synthesizer microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 150° C. for 20 min. The reaction mixture was diluted with EtOAc and filtered through Celite and the Celite was washed with DCM. The combined organic solutions were evaporated under reduced pressure. The crude residue was suspended in DCM and washed with saturated sodium bicarbonate followed by brine, water and dried over MgSO4. The organic solutions were evaporated under reduced pressure and the crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 95% MeOH in DCM to provide N-tert-butyl-5-(5-(cyclopropylcarbamoyl)-2-methylphenyl)thiophene-2-carboxamide (1.2 g). MS (ES+): 357 (M+H)+.

출처