Dichloromethane → 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxybenzyl)pyridin-3-yl)cyclopropanecarboxamide

HRID 2069350노트

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HRID 2069350 반응식
[Cl-].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][Zn+].C(Cl)Cl.[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3([C:27]([NH:29][C:30]4[CH:31]=[N:32][C:33](Br)=[CH:34][CH:35]=4)=[O:28])[CH2:26][CH2:25]3)=[CH:23][C:18]=2[O:17][CH2:16]1.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+].[NH4+].[Cl-]>C1COCC1>[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3([C:27]([NH:29][C:30]4[CH:31]=[N:32][C:33]([CH2:6][C:5]5[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=5[O:3][CH3:2])=[CH:34][CH:35]=4)=[O:28])[CH2:26][CH2:25]3)=[CH:23][C:18]=2[O:17][CH2:16]1

참가 물질

7

반응물 5

HCID 6344DichloromethaneHCID 8759EDTA disodium saltHCID 25517Ammonium ChlorideHCID 578561131-(benzo[d][1,3]dioxol-5-yl)-N-(6-bromopyridin-3-yl)cyclopropanecarboxamideHCID 178489474HCID 178489474, 화합물

생성물 1

HCID 442063271-(benzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxybenzyl)pyridin-3-yl)cyclopropanecarboxamide수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
150 °C

실험 절차

A solution of (2-methoxybenzyl)zinc(II) chloride (4.44 mL, 0.5 M, 2.20 mmol) in THF and (DPPF)2PdCl2.CH2Cl2 (45 mg, 0.056 mmol) was stirred at room temperature for 20 minutes. To this, a slurry of 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-bromopyridin-3-yl)cyclopropanecarboxamide (200 mg, 0.56 mmol) in THF (4 mL) was added and the reaction mixture was heated to 150° C. in a microwave reactor for 10 minutes. The resulting material was cooled to room temperature. Na2EDTA and saturated aqueous NH4Cl were added to the reaction and the mixture was stirred at room temperature for 30 minutes. The product was extracted using dichloromethane. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-(2-methoxybenzyl)pyridin-3-yl)cyclopropanecarboxamide (152 mg, 68%).

후처리

  1. temperatureThe resulting material was cooled to room temperature
  2. extractionThe product was extracted
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-e1cd911f609046eaa76d889af13d1490
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299099B2

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