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Cesium carbonate → Pyridin-2-YL(4-(3-(tetrahydro-2H-pyran-4-YL)pyridin-2-yloxy)phenyl)methanone

HRID 473691
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HRID 473691 반응식
F[C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.O>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][C:2]2[C:7]([CH:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:16][CH:17]=1)=[O:22]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 36317(4-Hydroxyphenyl)-2-pyridinylmethanoneHCID 593271552-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine

생성물 1

HCID 59374302Pyridin-2-YL(4-(3-(tetrahydro-2H-pyran-4-YL)pyridin-2-yloxy)phenyl)methanone

시약·촉매·용매 2

HCID 962Water용매
HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
180 °C

실험 절차

A glass microwave reaction vessel was charged with 2-fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine (0.4000 g, 2.207 mmol), (4-hydroxyphenyl)(pyridin-2-yl)methanone (0.660 g, 3.31 mmol), and cesium carbonate (2.158 g, 6.62 mmol) in N-Methyl-2-pyrrolidinone (7.36 mL). The reaction mixture was stirred and heated in a Biotage Initiator microwave reactor at 180° C. for 30 min. The reaction mixture was diluted with water and extracted with dichloromethane. The organic extract was washed with water, sat NaCl, dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography to give the title compound. MS (ESI, pos. ion) m/z: 361.0 (M+1). IC50 (uM) 0.5561.

후처리

  1. customA glass microwave reaction vessel
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography

출처 및 근거

ORD 기록
ord-dfcd981bcb7e4778b7d067114bab8919
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637500B2

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