참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | 1H-Indol-2-ylboronic acid | HCID 22567358 | — |
| 반응물 | 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane | HCID 86629376 | — |
| 촉매 | HCID 178418397 | HCID 178418397 | — |
| 용매 | Sodium Carbonate | HCID 10340 | — |
| 용매 | Toluene ethanol | HCID 21863594 | — |
| 생성물 | HCID 25261557 | HCID 25261557 | — |
반응 단계
A mixture of 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (80 mg, 0.27 mmol), 5-indoylboronic acid (66 mg, 0.41 mmol), and tetrakis(triphenylphosphine)palladium(0) (35 mg, 10 mol %) in toluene/ethanol (1:1, 3 mL) and 2 M aqueous sodium carbonate solution (1 mL) was heated in a Smith process vial in the microwave reactor for one hour at 120° C. The cooled mixture was acidified with concentrated hydrochloric acid and then concentrated to dryness under reduced pressure. The crude residue was purified via reverse-phase high performance liquid chromatography using a Phenomenex Prodigy 21 mm×250 mm column to provide 1-ethyl-6-(1H-indol-5-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine. MS (ES+): 375.2 (M+H)+
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08129371B2 |
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| 출처 데이터셋 | uspto-grants-2012_03 |
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| ORD ID | ord-ee7d283118cd470298de706ab91fda1a |
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| 출처 메모 | uspto-grants-2012_03 |
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