反応 #47853

反応方程式

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

収率 59.1%

溶媒

EtOAc

water

反応条件

後処理

1. 1
   ろ過filtered through Celite
2. 2
   洗浄the Celite was washed with DCM
3. 3
   その他The combined organic solutions were evaporated under reduced pressure
4. 4
   洗浄washed with saturated sodium bicarbonate
5. 5
   乾燥dried over MgSO4
6. 6
   その他The organic solutions were evaporated under reduced pressure
7. 7
   その他chromatographed through a Redi-Sep pre-packed silica gel column (40 g)
8. 8
   洗浄eluting with a gradient of 5% to 95% MeOH in DCM

実験手順

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)+.

出典