تفاعل #680092

معادلة التفاعل

222a

N-(5-Chloro-2-methoxypyridin-3-yl)-2-methylpyrimidin-4-amine

(3-(acetoxymethyl)-2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo-[1,2-a]pyrazin-2(6H)-yl)pyridin-4-yl)boronic acid

{3-[(Acetyloxy)methyl]-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-4-yl}boronic Acid

tricyclohexylphospine

Cs2CO3

→

222b

المردود 25.0%

(2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-{6-methoxy-5-[(2-methylpyrimidin-4-yl)amino]pyridin-3-yl}pyridin-3-yl)methyl Acetate

المردود 25.0%

المذيبات

water

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىA sealed tube equipped with a magnetic stirrer
2. 2
   أخرىAfter three cycles of vacuum/argon flush
3. 3
   ترشيحIt was then filtered
4. 4
   أخرىthe filtrate was evaporated in vacuo
5. 5
   أخرىThe residue was purified by silica-gel column chromatography
6. 6
   غسيلeluting with 30:1 ethyl acetate/methanol

الإجراء التجريبي

A sealed tube equipped with a magnetic stirrer was charged with 222a (550 mg, 2.2 mmol), (3-(acetoxymethyl)-2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo-[1,2-a]pyrazin-2(6H)-yl)pyridin-4-yl)boronic acid 199e (2.18 g, 5.5 mmol), Pd2(dba)3 (201 mg, 0.22 mmol), tricyclohexylphospine (84 mg, 0.30 mmol), Cs2CO3 (1.43 g, 4.4 mmol), dioxane (12 mL), and water (1 mL). After three cycles of vacuum/argon flush, the mixture was heated at 110° C. for 4 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 30:1 ethyl acetate/methanol to afford 222b (310 mg, 25%) as a yellow solid. MS-ESI: [M+H]+ 568.6

المصدر