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

HRID 473691
Notes
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Reaction equation

HRID 473691 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
180 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dfcd981bcb7e4778b7d067114bab8919
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637500B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes