Potassium Phosphate, Tribasic → HCID 58547005, 화합물

HRID 1850343노트

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HRID 1850343 반응식
Br[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:22][O:23][C:24]1[CH:29]=[C:28]([C:2]2[C:3]([CH:8]3[CH2:11][N:10]([C:12]4[CH:21]=[CH:20][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:13]=4)[CH2:9]3)=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:27]=[CH:26][CH:25]=1

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 58547111HCID 58547111, 화합물

생성물 1

HCID 58547005HCID 58547005, 화합물수율 36%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 2-[3-(3-bromo-pyridin-2-yl)-azetidin-1-yl]-quinoline (339 mg, 1 mmol), 3-methoxy-phenylboronic acid (167.2 mg, 1.1 mmol), K3PO4 (414 mg, 2.0 mmol) in dioxane (20 mL) and water (2 mL) was added Pd(dppf)Cl2 (36.6 mg, 0.05 mmol) then the reaction mixture was stirred at 90° C. under nitrogen atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by ISCO silica gel column (10% to 80% EtOAc in petroleum ether) to give 2-{3-[3-(3-methoxy-phenyl)-pyridin-2-yl]-azetidin-1-yl}-quinoline (132 mg, 0.36 mmol, yield 36%).

후처리

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. washwashed with EtOAc (50 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by ISCO silica gel column (10% to 80% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-e62810dfbf204dfca0247588b54d567c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957073B2

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