반응 #627077

반응 방정식

methyl (1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methanol

1-methyl-1H-indol-5-amine

potassium carbonate

(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)

→

desired product

수율 40.5%

(3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methanol

수율 40.5%

용매

dioxane

반응 조건

후처리

1. 1
   기타After being degassed by nitrogen bubbling
2. 2
   기타Volatiles were removed in vacuo
3. 3
   추출the resulting residue was extracted with ethyl acetate
4. 4
   건조The collected organic layer was dried over anhydrous sodium sulfate
5. 5
   농축concentrated in vacuo
6. 6
   기타The resulting residue was purified by recrystallization in acetonitrile

실험 절차

A round bottomed flask was charged with methyl (1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methanol (400 mg, 1.78 mmol), 1-methyl-1H-indol-5-amine (338 mg, 1.3 equiv.), potassium carbonate (0.74 g, 3.0 equiv), palladium acetate (40 mg, 0.1 equiv), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (Xantphos, 206 mg, 0.2 equiv.) and 40 mL of anhydrous dioxane. After being degassed by nitrogen bubbling, the reaction mixture was heated at 100° C. for 12 hours. Volatiles were removed in vacuo and then the resulting residue was extracted with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by recrystallization in acetonitrile to give 241 mg (36%) of the desired product as a brown solid. MS (ESI) m/z 335 [M+H]+.

출처