반응 #1133153

반응 방정식

cesium carbonate

9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene

2-amino-N,6-dimethoxybenzamide

N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine

→

2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-N,6-dimethoxy-benzamide

수율 74.6%

title compound

수율 74.6%

용매

dioxane

반응 조건

후처리

1. 1
   기타sealed
2. 2
   기타Argon was bubbled through the mixture for 5 minutes
3. 3
   온도to cool to room temperature
4. 4
   workup.ADDITIONdiluted with DCM and MeOH
5. 5
   workup.ADDITIONSilica gel was added
6. 6
   농축the mixture was concentrated
7. 7
   기타The crude product was purified by flash chromatography on silica gel (25 g)
8. 8
   세척eluting with 0 to 5% MeOH in EtOAc/DCM (1:1)
9. 9
   기타The solvent was evaporated to dryness
10. 10
    기타The residue was triturated in Et2O
11. 11
    여과the resulting precipitate was collected by filtration
12. 12
    세척washed with Et2O
13. 13
    기타dried to a constant weight

실험 절차

9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (34.1 mg, 0.06 mmol), palladium(II) acetate (7.93 mg, 0.04 mmol), 2-amino-N,6-dimethoxybenzamide (131 mg, 0.67 mmol), N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were weighed out in a microwave vial, sealed and dioxane (5 mL) was added. Argon was bubbled through the mixture for 5 minutes. The reaction was stirred at 90° C. overnight. The reaction mixture was allowed to cool to room temperature, diluted with DCM and MeOH. Silica gel was added and the mixture was concentrated. The crude product was purified by flash chromatography on silica gel (25 g) eluting with 0 to 5% MeOH in EtOAc/DCM (1:1). The solvent was evaporated to dryness. The residue was triturated in Et2O and the resulting precipitate was collected by filtration, washed with Et2O and dried to a constant weight to afford the title compound (131 mg, 74.1%) as a off-white solid. NMR Spectrum: (DMSOd6) 2.04 (s, 3H), 3.62 (s, 3H), 3.69 (s, 3H), 3.81 (s, 3H), 6.31 (bs, 1H), 6.89 (d, 1H), 7.06 (d, 1H), 7.43 (dd, 1H), 7.79 (s, 1H), 7.86 (s, 1H), 8.14 (s, 1H), 8.38 (s, 1H), 11.38 (s, 1H); Mass spectrum: MH+ 451.

출처