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Cesium carbonate → 4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-benzonitrile

HRID 2261756
Notes
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Reaction equation

HRID 2261756 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1.F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([CH3:28])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([CH3:28])[CH:21]=2)=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 38260554-Fluoro-2-methylbenzonitrileHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

Product 1

HCID 675281824-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-benzonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

To an ambient temperature solution of [2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-methanol (2.50 g, 8.76 mmol) in DMF (15 mL) is added 4-Fluoro-2-methyl-benzonitrile 1.18 g, 8.76 mmol), cesium carbonate (5.71 g, 17.53 mmol). The reaction mixture is heated to 80° C. overnight. The reaction mixture is concentrated and the residue is partitioned between Et2O and water. The aqueous layer is extracted with Et2O and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (2.13 g, 61%). 1H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H), 7.46-7.40 (m, 3H), 7.32 (dd, 1H, J=9.0, 7.3 Hz), 6.68-6.62 (m, 2H), 4.85 (s, 2H), 2.99 (sept, 1H, J=7.0 Hz), 2.46 (s, 3H), 1.31 (d, 6H, J=7.0 Hz).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between Et2O and water
  3. extractionThe aqueous layer is extracted with Et2O
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (0% to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-84c3b8eceec94005bfa1a38e6b3ee970
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846960B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes